# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1009888'
_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H39 N3 O12.50 Tb'
_chemical_formula_weight         848.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   10.913(3)
_cell_length_b                   16.542(4)
_cell_length_c                   19.793(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3573.2(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8594
_cell_measurement_theta_min      2.0579
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1716
_exptl_absorpt_coefficient_mu    2.046
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5037
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         4574
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18735
_diffrn_reflns_av_R_equivalents  0.0987
_diffrn_reflns_av_sigmaI/netI    0.0813
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3226
_reflns_number_gt                2751
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1435P)²+25.2326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3226
_refine_ls_number_parameters     216
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.2324
_refine_ls_wR_factor_gt          0.2161
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4177(10) 0.2500 1.0287(6) 0.024(2) Uani 1 2 d S . .
Tb1 Tb 0.29329(6) 0.2500 0.70436(3) 0.0262(3) Uani 1 2 d S . .
O1 O 0.1886(9) 0.2500 0.8056(5) 0.033(2) Uani 1 2 d S . .
O2 O -0.0069(10) 0.2500 0.8321(6) 0.049(3) Uani 1 2 d S . .
O4 O 0.3407(12) 0.2500 1.1501(6) 0.050(3) Uani 1 2 d S . .
H4A H 0.3463 0.2500 1.1914 0.074 Uiso 1 2 calc SR . .
O3 O 0.1431(12) 0.2500 1.1732(6) 0.056(3) Uani 1 2 d S . .
O5 O 0.3643(7) -0.1455(5) 1.1869(4) 0.044(2) Uani 1 1 d . . .
O6 O 0.2193(8) -0.1549(5) 1.1112(5) 0.049(2) Uani 1 1 d . . .
C1 C 0.1027(12) 0.2500 0.8466(7) 0.025(3) Uani 1 2 d S . .
C2 C 0.1337(13) 0.2500 0.9207(7) 0.030(3) Uani 1 2 d S . .
C3 C 0.0425(13) 0.2500 0.9697(8) 0.040(4) Uani 1 2 d S . .
H3 H -0.0396 0.2500 0.9573 0.048 Uiso 1 2 calc SR . .
C4 C 0.0750(13) 0.2500 1.0371(7) 0.034(3) Uani 1 2 d S . .
H4 H 0.0137 0.2500 1.0698 0.041 Uiso 1 2 calc SR . .
C5 C 0.1975(13) 0.2500 1.0576(7) 0.026(3) Uani 1 2 d S . .
C6 C 0.2895(12) 0.2500 1.0090(7) 0.025(3) Uani 1 2 d S . .
C7 C 0.2569(13) 0.2500 0.9388(7) 0.026(3) Uani 1 2 d S . .
H1 H 0.3175 0.2500 0.9058 0.031 Uiso 1 2 calc SR . .
C8 C 0.2229(15) 0.2500 1.1325(8) 0.037(4) Uani 1 2 d S . .
C9 C 0.4842(10) 0.1761(6) 1.0045(5) 0.033(2) Uani 1 1 d . . .
H9A H 0.5710 0.1816 1.0141 0.039 Uiso 1 1 calc R . .
H9B H 0.4743 0.1709 0.9560 0.039 Uiso 1 1 calc R . .
C10 C 0.4350(9) 0.1006(6) 1.0392(5) 0.029(2) Uani 1 1 d . . .
C11 C 0.4819(10) 0.0754(7) 1.1009(6) 0.041(3) Uani 1 1 d . . .
H11 H 0.5416 0.1065 1.1220 0.050 Uiso 1 1 calc R . .
C12 C 0.4424(10) 0.0053(7) 1.1316(6) 0.039(3) Uani 1 1 d . . .
H12 H 0.4758 -0.0099 1.1729 0.047 Uiso 1 1 calc R . .
C13 C 0.3531(9) -0.0432(6) 1.1015(5) 0.032(2) Uani 1 1 d . . .
C14 C 0.3050(9) -0.0171(7) 1.0402(6) 0.036(3) Uani 1 1 d . . .
H14 H 0.2445 -0.0479 1.0194 0.043 Uiso 1 1 calc R . .
C15 C 0.3444(10) 0.0529(6) 1.0094(5) 0.035(2) Uani 1 1 d . . .
H15 H 0.3103 0.0685 0.9684 0.043 Uiso 1 1 calc R . .
C16 C 0.3114(10) -0.1185(7) 1.1341(6) 0.036(2) Uani 1 1 d . . .
O1W O 0.3902(7) 0.1440(5) 0.7658(5) 0.056(2) Uani 1 1 d . . .
H1WB H 0.4512 0.1654 0.7857 0.067 Uiso 1 1 d R . .
H1WA H 0.3552 0.1143 0.7951 0.067 Uiso 1 1 d R . .
O7 O 0.2391(13) 0.0642(9) 0.8489(8) 0.121(5) Uiso 1 1 d D . .
C17 C 0.1593(13) 0.0171(9) 0.8485(8) 0.104(7) Uiso 1 1 d D . .
N2 N 0.1618(15) -0.0604(10) 0.8169(9) 0.125(7) Uiso 1 1 d D . .
C18 C 0.0440(16) 0.0238(11) 0.8913(10) 0.109(7) Uiso 1 1 d D . .
H18A H -0.0035 0.0710 0.8785 0.131 Uiso 1 1 calc R . .
H18B H 0.0644 0.0276 0.9389 0.131 Uiso 1 1 calc R . .
C20 C 0.044(2) -0.1016(13) 0.8216(12) 0.147(10) Uiso 1 1 d D . .
H20A H 0.0549 -0.1577 0.8347 0.176 Uiso 1 1 calc R . .
H20B H 0.0011 -0.0998 0.7787 0.176 Uiso 1 1 calc R . .
C19 C -0.028(2) -0.0548(16) 0.8763(16) 0.209(17) Uiso 1 1 d D . .
H19A H -0.0347 -0.0872 0.9169 0.251 Uiso 1 1 calc R . .
H19B H -0.1094 -0.0421 0.8603 0.251 Uiso 1 1 calc R . .
O4W O 0.097(4) 0.2500 1.311(2) 0.108(13) Uiso 0.50 2 d SP . .
H4WA H 0.0205 0.2500 1.3030 0.129 Uiso 0.50 2 d SPR . .
H4WB H 0.1130 0.2500 1.2668 0.129 Uiso 0.50 2 d SPR . .
C21 C 0.243(2) -0.0747(18) 0.7613(13) 0.176(13) Uiso 1 1 d D . .
H21A H 0.3173 -0.0447 0.7679 0.264 Uiso 1 1 calc R . .
H21B H 0.2043 -0.0575 0.7201 0.264 Uiso 1 1 calc R . .
H21C H 0.2613 -0.1313 0.7586 0.264 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.451(17) . ?
N1 C9 1.500(12) 7_565 ?
N1 C9 1.500(12) . ?
Tb1 O2 2.296(11) 6_657 ?
Tb1 O1 2.307(10) . ?
Tb1 O1W 2.382(8) 7_565 ?
Tb1 O1W 2.382(8) . ?
Tb1 O6 2.428(9) 2_554 ?
Tb1 O6 2.428(9) 8_665 ?
Tb1 O5 2.463(8) 8_665 ?
Tb1 O5 2.463(8) 2_554 ?
Tb1 C16 2.824(11) 8_665 ?
Tb1 C16 2.824(11) 2_554 ?
O1 C1 1.240(17) . ?
O2 C1 1.230(17) . ?
O2 Tb1 2.296(11) 6_557 ?
O4 C8 1.33(2) . ?
O4 H4A 0.8200 . ?
O3 C8 1.19(2) . ?
O5 C16 1.275(13) . ?
O5 Tb1 2.463(8) 2 ?
O6 C16 1.257(14) . ?
O6 Tb1 2.428(8) 2 ?
C1 C2 1.505(19) . ?
C2 C3 1.39(2) . ?
C2 C7 1.39(2) . ?
C3 C4 1.38(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.40(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.39(2) . ?
C5 C8 1.509(19) . ?
C6 C7 1.435(19) . ?
C7 H1 0.9300 . ?
C9 C10 1.523(14) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.389(15) . ?
C10 C15 1.396(15) . ?
C11 C12 1.377(16) . ?
C11 H11 0.9300 . ?
C12 C13 1.396(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(15) . ?
C13 C16 1.475(15) . ?
C14 C15 1.377(15) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 Tb1 2.824(11) 2 ?
O1W H1WB 0.8500 . ?
O1W H1WA 0.8499 . ?
O7 C17 1.169(9) . ?
C17 N2 1.426(9) . ?
C17 C18 1.520(9) . ?
N2 C21 1.432(9) . ?
N2 C20 1.459(9) . ?
C18 C19 1.547(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 C19 1.543(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
O4W H4WA 0.8500 . ?
O4W H4WB 0.8828 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C9 112.4(7) . 7_565 ?
C6 N1 C9 112.4(7) . . ?
C9 N1 C9 109.2(10) 7_565 . ?
O2 Tb1 O1 138.0(4) 6_657 . ?
O2 Tb1 O1W 74.9(3) 6_657 7_565 ?
O1 Tb1 O1W 77.1(3) . 7_565 ?
O2 Tb1 O1W 74.9(3) 6_657 . ?
O1 Tb1 O1W 77.1(3) . . ?
O1W Tb1 O1W 94.8(5) 7_565 . ?
O2 Tb1 O6 79.3(3) 6_657 2_554 ?
O1 Tb1 O6 129.2(2) . 2_554 ?
O1W Tb1 O6 152.9(3) 7_565 2_554 ?
O1W Tb1 O6 86.3(3) . 2_554 ?
O2 Tb1 O6 79.3(3) 6_657 8_665 ?
O1 Tb1 O6 129.2(2) . 8_665 ?
O1W Tb1 O6 86.3(3) 7_565 8_665 ?
O1W Tb1 O6 152.9(3) . 8_665 ?
O6 Tb1 O6 80.8(4) 2_554 8_665 ?
O2 Tb1 O5 128.2(2) 6_657 8_665 ?
O1 Tb1 O5 77.1(2) . 8_665 ?
O1W Tb1 O5 82.3(3) 7_565 8_665 ?
O1W Tb1 O5 154.0(3) . 8_665 ?
O6 Tb1 O5 108.0(3) 2_554 8_665 ?
O6 Tb1 O5 53.1(2) 8_665 8_665 ?
O2 Tb1 O5 128.2(2) 6_657 2_554 ?
O1 Tb1 O5 77.1(2) . 2_554 ?
O1W Tb1 O5 154.0(3) 7_565 2_554 ?
O1W Tb1 O5 82.3(3) . 2_554 ?
O6 Tb1 O5 53.1(3) 2_554 2_554 ?
O6 Tb1 O5 108.0(3) 8_665 2_554 ?
O5 Tb1 O5 89.1(4) 8_665 2_554 ?
O2 Tb1 C16 103.3(3) 6_657 8_665 ?
O1 Tb1 C16 103.2(3) . 8_665 ?
O1W Tb1 C16 82.2(3) 7_565 8_665 ?
O1W Tb1 C16 176.8(3) . 8_665 ?
O6 Tb1 C16 95.9(3) 2_554 8_665 ?
O6 Tb1 C16 26.3(3) 8_665 8_665 ?
O5 Tb1 C16 26.8(3) 8_665 8_665 ?
O5 Tb1 C16 100.9(3) 2_554 8_665 ?
O2 Tb1 C16 103.3(3) 6_657 2_554 ?
O1 Tb1 C16 103.2(3) . 2_554 ?
O1W Tb1 C16 176.8(3) 7_565 2_554 ?
O1W Tb1 C16 82.2(3) . 2_554 ?
O6 Tb1 C16 26.3(3) 2_554 2_554 ?
O6 Tb1 C16 95.9(3) 8_665 2_554 ?
O5 Tb1 C16 100.9(3) 8_665 2_554 ?
O5 Tb1 C16 26.8(3) 2_554 2_554 ?
C16 Tb1 C16 100.8(4) 8_665 2_554 ?
C1 O1 Tb1 160.5(9) . . ?
C1 O2 Tb1 175.2(11) . 6_557 ?
C8 O4 H4A 109.5 . . ?
C16 O5 Tb1 92.5(6) . 2 ?
C16 O6 Tb1 94.7(7) . 2 ?
O2 C1 O1 125.7(13) . . ?
O2 C1 C2 116.5(13) . . ?
O1 C1 C2 117.8(11) . . ?
C3 C2 C7 120.7(14) . . ?
C3 C2 C1 121.3(13) . . ?
C7 C2 C1 118.0(12) . . ?
C4 C3 C2 119.4(14) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.7(13) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.5(13) . . ?
C6 C5 C8 123.2(13) . . ?
C4 C5 C8 117.4(13) . . ?
C5 C6 C7 119.3(12) . . ?
C5 C6 N1 120.8(12) . . ?
C7 C6 N1 119.9(12) . . ?
C2 C7 C6 119.4(13) . . ?
C2 C7 H1 120.3 . . ?
C6 C7 H1 120.3 . . ?
O3 C8 O4 122.0(14) . . ?
O3 C8 C5 122.2(15) . . ?
O4 C8 C5 115.8(13) . . ?
N1 C9 C10 110.7(8) . . ?
N1 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C15 117.6(9) . . ?
C11 C10 C9 120.8(10) . . ?
C15 C10 C9 121.6(9) . . ?
C12 C11 C10 121.7(10) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 121.0(10) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 117.2(10) . . ?
C14 C13 C16 121.8(10) . . ?
C12 C13 C16 121.0(10) . . ?
C15 C14 C13 121.9(10) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C10 120.7(10) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O6 C16 O5 119.4(10) . . ?
O6 C16 C13 119.6(10) . . ?
O5 C16 C13 120.9(10) . . ?
O6 C16 Tb1 59.0(6) . 2 ?
O5 C16 Tb1 60.6(6) . 2 ?
C13 C16 Tb1 172.4(7) . 2 ?
Tb1 O1W H1WB 106.1 . . ?
Tb1 O1W H1WA 125.0 . . ?
H1WB O1W H1WA 106.0 . . ?
O7 C17 N2 126.0(13) . . ?
O7 C17 C18 124.3(12) . . ?
N2 C17 C18 109.0(8) . . ?
C17 N2 C21 119.8(13) . . ?
C17 N2 C20 112.1(9) . . ?
C21 N2 C20 121.1(14) . . ?
C17 C18 C19 104.4(8) . . ?
C17 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C17 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
N2 C20 C19 104.8(9) . . ?
N2 C20 H20A 110.8 . . ?
C19 C20 H20A 110.8 . . ?
N2 C20 H20B 110.8 . . ?
C19 C20 H20B 110.8 . . ?
H20A C20 H20B 108.9 . . ?
C20 C19 C18 107.5(9) . . ?
C20 C19 H19A 110.2 . . ?
C18 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
C18 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
H4WA O4W H4WB 91.1 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O7 0.85 1.85 2.678(17) 163.4 .
O1W H1WB O5 0.85 2.11 2.838(11) 143.2 5_657
O4W H4WA O4 0.85 2.17 2.91(5) 144.6 6_558
O4W H4WB O3 0.88 1.88 2.76(4) 178.8 .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.872
_refine_diff_density_min         -1.107
_refine_diff_density_rms         0.216
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1009889'
_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 N O14.50 Tb'
_chemical_formula_weight         722.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   10.932(3)
_cell_length_b                   16.713(4)
_cell_length_c                   18.893(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3452.0(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7978
_cell_measurement_theta_min      2.1519
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1444
_exptl_absorpt_coefficient_mu    2.107
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         4409
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23060
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3131
_reflns_number_gt                3018
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1771P)²+14.9095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3131
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.2437
_refine_ls_wR_factor_gt          0.2382
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4244(9) 0.2500 1.0350(5) 0.037(2) Uani 1 2 d S . .
Tb1 Tb 0.29423(5) 0.2500 0.70461(3) 0.0377(3) Uani 1 2 d S . .
O1 O 0.1853(10) 0.2500 0.8070(5) 0.054(3) Uani 1 2 d S . .
O2 O -0.0111(8) 0.2500 0.8362(5) 0.059(3) Uani 1 2 d S . .
O4 O 0.3560(11) 0.2500 1.1638(5) 0.068(3) Uani 1 2 d S . .
H4A H 0.3640 0.2500 1.2069 0.103 Uiso 1 2 calc SR . .
O3 O 0.1592(19) 0.2500 1.1926(7) 0.168(12) Uani 1 2 d S . .
O5 O 0.3629(7) -0.1498(5) 1.1838(4) 0.067(2) Uani 1 1 d . . .
O6 O 0.2147(7) -0.1533(5) 1.1081(5) 0.071(2) Uani 1 1 d . . .
C1 C 0.1004(11) 0.2500 0.8530(7) 0.044(3) Uani 1 2 d S . .
C2 C 0.1368(10) 0.2500 0.9280(7) 0.040(3) Uani 1 2 d S . .
C3 C 0.0471(13) 0.2500 0.9811(8) 0.066(4) Uani 1 2 d S . .
H3 H -0.0356 0.2500 0.9696 0.079 Uiso 1 2 calc SR . .
C4 C 0.0848(14) 0.2500 1.0511(8) 0.080(6) Uani 1 2 d S . .
H4 H 0.0257 0.2500 1.0865 0.096 Uiso 1 2 calc SR . .
C5 C 0.2055(12) 0.2500 1.0703(8) 0.056(4) Uani 1 2 d S . .
C6 C 0.2933(9) 0.2500 1.0184(7) 0.036(3) Uani 1 2 d S . .
C7 C 0.2576(11) 0.2500 0.9447(6) 0.035(2) Uani 1 2 d S . .
H1 H 0.3165 0.2500 0.9092 0.042 Uiso 1 2 calc SR . .
C8 C 0.241(2) 0.2500 1.1479(9) 0.078(5) Uani 1 2 d S . .
C9 C 0.4883(8) 0.1754(5) 1.0092(5) 0.044(2) Uani 1 1 d . . .
H9A H 0.4805 0.1721 0.9582 0.053 Uiso 1 1 calc R . .
H9B H 0.5747 0.1791 1.0205 0.053 Uiso 1 1 calc R . .
C10 C 0.4365(8) 0.1005(5) 1.0421(5) 0.045(2) Uani 1 1 d . . .
C11 C 0.4744(9) 0.0752(6) 1.1093(5) 0.054(2) Uani 1 1 d . . .
H11 H 0.5286 0.1066 1.1352 0.064 Uiso 1 1 calc R . .
C12 C 0.4331(9) 0.0057(6) 1.1368(5) 0.053(2) Uani 1 1 d . . .
H12 H 0.4615 -0.0104 1.1810 0.063 Uiso 1 1 calc R . .
C13 C 0.3504(8) -0.0421(5) 1.1018(5) 0.0424(19) Uani 1 1 d . . .
C14 C 0.3081(8) -0.0164(6) 1.0366(6) 0.050(2) Uani 1 1 d . . .
H14 H 0.2502 -0.0468 1.0126 0.060 Uiso 1 1 calc R . .
C15 C 0.3508(9) 0.0543(5) 1.0066(5) 0.050(2) Uani 1 1 d . . .
H15 H 0.3218 0.0706 0.9626 0.060 Uiso 1 1 calc R . .
C16 C 0.3078(7) -0.1185(6) 1.1317(5) 0.046(2) Uani 1 1 d . . .
O1W O 0.3915(6) 0.1475(5) 0.7715(5) 0.074(2) Uani 1 1 d . . .
H1WB H 0.4759 0.1433 0.7583 0.111 Uiso 1 1 d R . .
H1WA H 0.3868 0.1593 0.8189 0.111 Uiso 1 1 d R . .
O2W O 0.7704(16) -0.0431(12) 1.1637(10) 0.165(6) Uiso 1 1 d . . .
H2WA H 0.8428 -0.0425 1.1407 0.198 Uiso 1 1 d R . .
H2WB H 0.7175 -0.0756 1.1834 0.198 Uiso 1 1 d R . .
O3W O 0.983(2) -0.0395(19) 1.0998(15) 0.273(12) Uiso 1 1 d . . .
H3WC H 1.0301 -0.0424 1.1355 0.327 Uiso 1 1 d R . .
H3WB H 1.0287 -0.0597 1.0682 0.327 Uiso 1 1 d R . .
O4W O 0.663(4) 0.2500 1.1464(19) 0.118(10) Uiso 0.50 2 d SP . .
H4WA H 0.5846 0.2500 1.1492 0.142 Uiso 0.50 2 d SPR . .
H4WB H 0.6688 0.2865 1.1775 0.142 Uiso 0.25 1 d PR . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.468(14) . ?
N1 C9 1.509(10) 7_565 ?
N1 C9 1.509(10) . ?
Tb1 O2 2.264(8) 6_657 ?
Tb1 O1 2.272(10) . ?
Tb1 O1W 2.380(7) 7_565 ?
Tb1 O1W 2.380(7) . ?
Tb1 O5 2.431(7) 2_554 ?
Tb1 O5 2.431(7) 8_665 ?
Tb1 O6 2.439(8) 2_554 ?
Tb1 O6 2.439(8) 8_665 ?
Tb1 C16 2.824(10) 2_554 ?
Tb1 C16 2.824(10) 8_665 ?
O1 C1 1.271(16) . ?
O2 C1 1.259(15) . ?
O2 Tb1 2.264(8) 6_557 ?
O4 C8 1.29(3) . ?
O4 H4A 0.8200 . ?
O3 C8 1.23(2) . ?
O5 C16 1.268(12) . ?
O5 Tb1 2.431(7) 2 ?
O6 C16 1.255(11) . ?
O6 Tb1 2.439(8) 2 ?
C1 C2 1.471(18) . ?
C2 C7 1.358(18) . ?
C2 C3 1.403(18) . ?
C3 C4 1.39(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.37(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(18) . ?
C5 C8 1.52(2) . ?
C6 C7 1.447(17) . ?
C7 H1 0.9300 . ?
C9 C10 1.508(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.388(13) . ?
C10 C11 1.401(13) . ?
C11 C12 1.350(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(13) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(14) . ?
C13 C16 1.472(13) . ?
C14 C15 1.391(14) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 Tb1 2.824(10) 2 ?
O1W H1WB 0.9583 . ?
O1W H1WA 0.9189 . ?
O2W H2WA 0.9029 . ?
O2W H2WB 0.8754 . ?
O3W H3WC 0.8500 . ?
O3W H3WB 0.8500 . ?
O4W H4WA 0.8531 . ?
O4W H4WB 0.8502 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C9 112.5(6) . 7_565 ?
C6 N1 C9 112.5(6) . . ?
C9 N1 C9 111.3(9) 7_565 . ?
O2 Tb1 O1 141.5(4) 6_657 . ?
O2 Tb1 O1W 76.2(3) 6_657 7_565 ?
O1 Tb1 O1W 77.4(3) . 7_565 ?
O2 Tb1 O1W 76.2(2) 6_657 . ?
O1 Tb1 O1W 77.4(3) . . ?
O1W Tb1 O1W 92.1(5) 7_565 . ?
O2 Tb1 O5 127.6(2) 6_657 2_554 ?
O1 Tb1 O5 76.5(3) . 2_554 ?
O1W Tb1 O5 153.8(3) 7_565 2_554 ?
O1W Tb1 O5 84.6(3) . 2_554 ?
O2 Tb1 O5 127.6(2) 6_657 8_665 ?
O1 Tb1 O5 76.5(2) . 8_665 ?
O1W Tb1 O5 84.6(3) 7_565 8_665 ?
O1W Tb1 O5 153.8(3) . 8_665 ?
O5 Tb1 O5 87.1(4) 2_554 8_665 ?
O2 Tb1 O6 77.5(2) 6_657 2_554 ?
O1 Tb1 O6 128.0(2) . 2_554 ?
O1W Tb1 O6 153.1(3) 7_565 2_554 ?
O1W Tb1 O6 86.4(3) . 2_554 ?
O5 Tb1 O6 52.7(2) 2_554 2_554 ?
O5 Tb1 O6 107.9(3) 8_665 2_554 ?
O2 Tb1 O6 77.5(3) 6_657 8_665 ?
O1 Tb1 O6 128.0(2) . 8_665 ?
O1W Tb1 O6 86.4(3) 7_565 8_665 ?
O1W Tb1 O6 153.1(3) . 8_665 ?
O5 Tb1 O6 107.9(3) 2_554 8_665 ?
O5 Tb1 O6 52.7(2) 8_665 8_665 ?
O6 Tb1 O6 83.0(5) 2_554 8_665 ?
O2 Tb1 C16 101.9(2) 6_657 2_554 ?
O1 Tb1 C16 102.0(3) . 2_554 ?
O1W Tb1 C16 174.9(3) 7_565 2_554 ?
O1W Tb1 C16 82.8(3) . 2_554 ?
O5 Tb1 C16 26.6(2) 2_554 2_554 ?
O5 Tb1 C16 100.3(3) 8_665 2_554 ?
O6 Tb1 C16 26.3(2) 2_554 2_554 ?
O6 Tb1 C16 97.8(3) 8_665 2_554 ?
O2 Tb1 C16 101.9(2) 6_657 8_665 ?
O1 Tb1 C16 102.0(2) . 8_665 ?
O1W Tb1 C16 82.8(3) 7_565 8_665 ?
O1W Tb1 C16 174.9(3) . 8_665 ?
O5 Tb1 C16 100.3(3) 2_554 8_665 ?
O5 Tb1 C16 26.6(2) 8_665 8_665 ?
O6 Tb1 C16 97.8(3) 2_554 8_665 ?
O6 Tb1 C16 26.3(2) 8_665 8_665 ?
C16 Tb1 C16 102.2(4) 2_554 8_665 ?
C1 O1 Tb1 164.7(9) . . ?
C1 O2 Tb1 174.7(9) . 6_557 ?
C8 O4 H4A 109.5 . . ?
C16 O5 Tb1 94.3(6) . 2 ?
C16 O6 Tb1 94.2(6) . 2 ?
O2 C1 O1 122.3(12) . . ?
O2 C1 C2 120.3(11) . . ?
O1 C1 C2 117.4(11) . . ?
C7 C2 C3 120.9(12) . . ?
C7 C2 C1 119.1(11) . . ?
C3 C2 C1 120.0(11) . . ?
C4 C3 C2 118.3(13) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 122.7(13) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 119.0(14) . . ?
C4 C5 C8 120.2(14) . . ?
C6 C5 C8 120.8(14) . . ?
C5 C6 C7 120.0(11) . . ?
C5 C6 N1 122.0(12) . . ?
C7 C6 N1 118.0(10) . . ?
C2 C7 C6 119.1(11) . . ?
C2 C7 H1 120.5 . . ?
C6 C7 H1 120.5 . . ?
O3 C8 O4 123.3(18) . . ?
O3 C8 C5 119(2) . . ?
O4 C8 C5 118.2(14) . . ?
C10 C9 N1 112.3(7) . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
N1 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C15 C10 C11 118.1(8) . . ?
C15 C10 C9 121.1(8) . . ?
C11 C10 C9 120.8(8) . . ?
C12 C11 C10 120.6(9) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 122.2(9) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 117.9(8) . . ?
C12 C13 C16 121.8(8) . . ?
C14 C13 C16 120.4(8) . . ?
C13 C14 C15 121.0(8) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 120.1(9) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
O6 C16 O5 118.0(9) . . ?
O6 C16 C13 121.5(9) . . ?
O5 C16 C13 120.5(8) . . ?
O6 C16 Tb1 59.5(5) . 2 ?
O5 C16 Tb1 59.1(5) . 2 ?
C13 C16 Tb1 170.9(7) . 2 ?
Tb1 O1W H1WB 110.1 . . ?
Tb1 O1W H1WA 109.7 . . ?
H1WB O1W H1WA 108.9 . . ?
H2WA O2W H2WB 142.2 . . ?
H3WC O3W H3WB 100.1 . . ?
H4WA O4W H4WB 92.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WB O5 0.96 2.08 2.815(10) 132.5 5_657
O2W H2WA O3W 0.90 1.72 2.62(3) 177.8 .
O2W H2WB O1W 0.88 1.89 2.77(2) 177.5 5_657
O4W H4WA O4 0.85 2.51 3.37(4) 177.2 .
O4W H4WB O3 0.85 2.53 3.04(4) 119.7 6_658

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.263
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.191
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1009890'
_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H35 N3 O12.50 Tb'
_chemical_formula_weight         796.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   10.902(9)
_cell_length_b                   16.715(12)
_cell_length_c                   19.201(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3499(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9828
_cell_measurement_theta_min      2.1213
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1604
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7862
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         4473
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21857
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3171
_reflns_number_gt                2767
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1975P)²+9.4897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0009(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3171
_refine_ls_number_parameters     221
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.2551
_refine_ls_wR_factor_gt          0.2408
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0775(8) 0.2500 0.4633(6) 0.048(2) Uani 1 2 d S . .
Tb1 Tb -0.20767(5) 0.2500 0.79635(3) 0.0435(4) Uani 1 2 d S . .
O1 O -0.3108(10) 0.2500 0.6941(5) 0.058(3) Uani 1 2 d S . .
O2 O -0.5100(7) 0.2500 0.6640(5) 0.060(2) Uani 1 2 d S . .
O4 O -0.1505(11) 0.2500 0.3383(6) 0.074(3) Uani 1 2 d S . .
H4A H -0.1456 0.2500 0.2957 0.111 Uiso 1 2 calc SR . .
O3 O -0.3521(17) 0.2500 0.3149(8) 0.112(5) Uani 1 2 d S . .
O5 O -0.1349(6) -0.1480(4) 0.3135(4) 0.0616(18) Uani 1 1 d . . .
O6 O -0.2799(6) -0.1555(5) 0.3932(4) 0.067(2) Uani 1 1 d . . .
C1 C -0.3935(13) 0.2500 0.6514(8) 0.055(3) Uani 1 2 d S . .
C2 C -0.3650(10) 0.2500 0.5715(7) 0.045(3) Uani 1 2 d S . .
C3 C -0.4556(12) 0.2500 0.5229(9) 0.067(4) Uani 1 2 d S . .
H3 H -0.5379 0.2500 0.5358 0.080 Uiso 1 2 calc SR . .
C4 C -0.4213(14) 0.2500 0.4544(10) 0.076(5) Uani 1 2 d S . .
H4 H -0.4817 0.2500 0.4203 0.091 Uiso 1 2 calc SR . .
C5 C -0.2980(11) 0.2500 0.4342(8) 0.056(3) Uani 1 2 d S . .
C6 C -0.2084(9) 0.2500 0.4859(8) 0.045(3) Uani 1 2 d S . .
C7 C -0.2421(11) 0.2500 0.5536(7) 0.046(3) Uani 1 2 d S . .
H1 H -0.1825 0.2500 0.5883 0.056 Uiso 1 2 calc SR . .
C8 C -0.2697(16) 0.2500 0.3573(11) 0.076(5) Uani 1 2 d S . .
C9 C -0.0140(8) 0.1767(5) 0.4911(5) 0.052(2) Uani 1 1 d . . .
H9A H -0.0252 0.1740 0.5412 0.062 Uiso 1 1 calc R . .
H9B H 0.0733 0.1806 0.4818 0.062 Uiso 1 1 calc R . .
C10 C -0.0646(7) 0.1004(5) 0.4576(5) 0.050(2) Uani 1 1 d . . .
C11 C -0.0196(9) 0.0758(6) 0.3933(6) 0.063(3) Uani 1 1 d . . .
H11 H 0.0385 0.1065 0.3701 0.075 Uiso 1 1 calc R . .
C12 C -0.0623(9) 0.0047(5) 0.3640(6) 0.057(2) Uani 1 1 d . . .
H12 H -0.0335 -0.0110 0.3205 0.068 Uiso 1 1 calc R . .
C13 C -0.1464(7) -0.0428(5) 0.3983(5) 0.048(2) Uani 1 1 d . . .
C14 C -0.1918(8) -0.0174(6) 0.4628(6) 0.056(3) Uani 1 1 d . . .
H14 H -0.2501 -0.0480 0.4860 0.068 Uiso 1 1 calc R . .
C15 C -0.1492(9) 0.0549(5) 0.4928(6) 0.059(2) Uani 1 1 d . . .
H15 H -0.1783 0.0715 0.5360 0.071 Uiso 1 1 calc R . .
C16 C -0.1878(8) -0.1179(5) 0.3676(6) 0.049(2) Uani 1 1 d . . .
O1W O -0.1090(6) 0.1468(4) 0.7321(5) 0.074(2) Uani 1 1 d . . .
H1WA H -0.1420 0.1211 0.6988 0.088 Uiso 1 1 d R . .
H1WB H -0.0246 0.1426 0.7454 0.110 Uiso 1 1 d R . .
O4W O -0.373(5) 0.2500 0.171(3) 0.172(17) Uiso 0.50 2 d SP . .
H4WA H -0.4499 0.2500 0.1764 0.206 Uiso 0.50 2 d SPR . .
H4WB H -0.3648 0.2500 0.2170 0.206 Uiso 0.50 2 d SPR . .
N2 N -0.4105(16) -0.0429(11) 0.6619(7) 0.175(8) Uiso 1 1 d D . .
O7 O -0.2452(19) 0.0408(16) 0.6714(13) 0.215(8) Uiso 1 1 d D . .
C17 C -0.5382(18) -0.049(2) 0.6358(13) 0.155(12) Uiso 0.67 1 d PD A 1
H17A H -0.5725 -0.0994 0.6493 0.233 Uiso 0.67 1 calc PR A 1
H17B H -0.5383 -0.0446 0.5859 0.233 Uiso 0.67 1 calc PR A 1
H17C H -0.5865 -0.0063 0.6553 0.233 Uiso 0.67 1 calc PR A 1
C18 C -0.355(4) -0.1146(15) 0.6933(15) 0.198(19) Uiso 0.67 1 d PD A 1
H18A H -0.3097 -0.0996 0.7341 0.298 Uiso 0.67 1 calc PR A 1
H18B H -0.3010 -0.1394 0.6603 0.298 Uiso 0.67 1 calc PR A 1
H18C H -0.4186 -0.1516 0.7060 0.298 Uiso 0.67 1 calc PR A 1
C19 C -0.3477(19) 0.0340(11) 0.6574(12) 0.105(7) Uiso 0.67 1 d PD A 1
H19A H -0.3914 0.0787 0.6428 0.126 Uiso 0.67 1 calc PR A 1
C17A C -0.458(5) -0.1247(18) 0.674(2) 0.21(4) Uiso 0.33 1 d PD A 2
H17D H -0.4008 -0.1542 0.7019 0.317 Uiso 0.33 1 calc PR A 2
H17E H -0.4686 -0.1513 0.6300 0.317 Uiso 0.33 1 calc PR A 2
H17F H -0.5355 -0.1217 0.6975 0.317 Uiso 0.33 1 calc PR A 2
C18A C -0.477(3) 0.019(2) 0.6210(18) 0.108(15) Uiso 0.33 1 d PD A 2
H18D H -0.4239 0.0643 0.6140 0.162 Uiso 0.33 1 calc PR A 2
H18E H -0.5487 0.0354 0.6458 0.162 Uiso 0.33 1 calc PR A 2
H18F H -0.4997 -0.0028 0.5766 0.162 Uiso 0.33 1 calc PR A 2
C19A C -0.287(3) -0.022(2) 0.689(2) 0.15(3) Uiso 0.33 1 d PD A 2
H19B H -0.2447 -0.0565 0.7190 0.181 Uiso 0.33 1 calc PR A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.491(14) . ?
N1 C9 1.505(10) 7_565 ?
N1 C9 1.505(10) . ?
Tb1 O1 2.262(10) . ?
Tb1 O2 2.286(8) 6_657 ?
Tb1 O1W 2.378(7) 7_565 ?
Tb1 O1W 2.378(7) . ?
Tb1 O5 2.442(7) 2_455 ?
Tb1 O5 2.442(7) 8_566 ?
Tb1 O6 2.443(7) 8_566 ?
Tb1 O6 2.443(7) 2_455 ?
Tb1 C16 2.837(9) 2_455 ?
Tb1 C16 2.837(9) 8_566 ?
O1 C1 1.219(18) . ?
O2 C1 1.292(15) . ?
O2 Tb1 2.286(8) 6_557 ?
O4 C8 1.35(2) . ?
O4 H4A 0.8200 . ?
O3 C8 1.21(2) . ?
O5 C16 1.290(12) . ?
O5 Tb1 2.442(7) 2_454 ?
O6 C16 1.283(11) . ?
O6 Tb1 2.443(7) 2_454 ?
C1 C2 1.566(19) . ?
C2 C3 1.359(19) . ?
C2 C7 1.383(18) . ?
C3 C4 1.37(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.40(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(19) . ?
C5 C8 1.51(3) . ?
C6 C7 1.35(2) . ?
C7 H1 0.9300 . ?
C9 C10 1.532(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.373(13) . ?
C10 C11 1.389(14) . ?
C11 C12 1.394(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(13) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(14) . ?
C13 C16 1.459(12) . ?
C14 C15 1.417(13) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 Tb1 2.837(9) 2_454 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.9574 . ?
O4W H4WA 0.8500 . ?
O4W H4WB 0.8884 . ?
N2 C19 1.458(10) . ?
N2 C18 1.472(10) . ?
N2 C17A 1.481(10) . ?
N2 C17 1.483(10) . ?
N2 C19A 1.484(10) . ?
N2 C18A 1.485(10) . ?
O7 C19 1.155(18) . ?
O7 C19A 1.20(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9300 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C18A H18D 0.9600 . ?
C18A H18E 0.9600 . ?
C18A H18F 0.9600 . ?
C19A H19B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C9 109.7(7) . 7_565 ?
C6 N1 C9 109.7(7) . . ?
C9 N1 C9 109.0(9) 7_565 . ?
O1 Tb1 O2 139.3(4) . 6_657 ?
O1 Tb1 O1W 77.0(3) . 7_565 ?
O2 Tb1 O1W 75.3(2) 6_657 7_565 ?
O1 Tb1 O1W 77.0(3) . . ?
O2 Tb1 O1W 75.3(2) 6_657 . ?
O1W Tb1 O1W 93.0(4) 7_565 . ?
O1 Tb1 O5 76.6(3) . 2_455 ?
O2 Tb1 O5 128.1(2) 6_657 2_455 ?
O1W Tb1 O5 153.5(3) 7_565 2_455 ?
O1W Tb1 O5 83.2(3) . 2_455 ?
O1 Tb1 O5 76.6(3) . 8_566 ?
O2 Tb1 O5 128.1(2) 6_657 8_566 ?
O1W Tb1 O5 83.2(3) 7_565 8_566 ?
O1W Tb1 O5 153.5(3) . 8_566 ?
O5 Tb1 O5 88.6(4) 2_455 8_566 ?
O1 Tb1 O6 129.3(2) . 8_566 ?
O2 Tb1 O6 78.4(2) 6_657 8_566 ?
O1W Tb1 O6 87.2(3) 7_565 8_566 ?
O1W Tb1 O6 152.7(2) . 8_566 ?
O5 Tb1 O6 108.0(3) 2_455 8_566 ?
O5 Tb1 O6 53.6(2) 8_566 8_566 ?
O1 Tb1 O6 129.3(2) . 2_455 ?
O2 Tb1 O6 78.4(2) 6_657 2_455 ?
O1W Tb1 O6 152.7(2) 7_565 2_455 ?
O1W Tb1 O6 87.2(3) . 2_455 ?
O5 Tb1 O6 53.6(2) 2_455 2_455 ?
O5 Tb1 O6 108.0(3) 8_566 2_455 ?
O6 Tb1 O6 80.5(4) 8_566 2_455 ?
O1 Tb1 C16 102.6(3) . 2_455 ?
O2 Tb1 C16 102.6(2) 6_657 2_455 ?
O1W Tb1 C16 175.3(3) 7_565 2_455 ?
O1W Tb1 C16 82.4(3) . 2_455 ?
O5 Tb1 C16 27.0(2) 2_455 2_455 ?
O5 Tb1 C16 101.3(3) 8_566 2_455 ?
O6 Tb1 C16 96.5(3) 8_566 2_455 ?
O6 Tb1 C16 26.8(3) 2_455 2_455 ?
O1 Tb1 C16 102.6(3) . 8_566 ?
O2 Tb1 C16 102.6(2) 6_657 8_566 ?
O1W Tb1 C16 82.4(3) 7_565 8_566 ?
O1W Tb1 C16 175.3(3) . 8_566 ?
O5 Tb1 C16 101.3(3) 2_455 8_566 ?
O5 Tb1 C16 27.0(2) 8_566 8_566 ?
O6 Tb1 C16 26.8(3) 8_566 8_566 ?
O6 Tb1 C16 96.5(3) 2_455 8_566 ?
C16 Tb1 C16 102.2(4) 2_455 8_566 ?
C1 O1 Tb1 162.0(10) . . ?
C1 O2 Tb1 171.2(10) . 6_557 ?
C8 O4 H4A 109.5 . . ?
C16 O5 Tb1 93.8(5) . 2_454 ?
C16 O6 Tb1 94.0(6) . 2_454 ?
O1 C1 O2 127.1(13) . . ?
O1 C1 C2 120.8(11) . . ?
O2 C1 C2 112.2(12) . . ?
C3 C2 C7 122.3(13) . . ?
C3 C2 C1 121.9(11) . . ?
C7 C2 C1 115.8(11) . . ?
C2 C3 C4 117.4(12) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C3 C4 C5 122.1(13) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 118.4(15) . . ?
C6 C5 C8 123.7(12) . . ?
C4 C5 C8 118.0(14) . . ?
C7 C6 C5 119.7(11) . . ?
C7 C6 N1 122.6(12) . . ?
C5 C6 N1 117.7(12) . . ?
C6 C7 C2 120.1(12) . . ?
C6 C7 H1 119.9 . . ?
C2 C7 H1 119.9 . . ?
O3 C8 O4 122(2) . . ?
O3 C8 C5 120.4(19) . . ?
O4 C8 C5 117.5(13) . . ?
N1 C9 C10 111.3(7) . . ?
N1 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C15 C10 C11 120.7(8) . . ?
C15 C10 C9 119.7(9) . . ?
C11 C10 C9 119.5(8) . . ?
C10 C11 C12 119.6(9) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 121.2(10) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 118.9(8) . . ?
C12 C13 C16 120.5(9) . . ?
C14 C13 C16 120.6(8) . . ?
C13 C14 C15 120.2(9) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.5(9) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
O6 C16 O5 117.8(8) . . ?
O6 C16 C13 120.6(9) . . ?
O5 C16 C13 121.5(8) . . ?
O6 C16 Tb1 59.2(5) . 2_454 ?
O5 C16 Tb1 59.2(5) . 2_454 ?
C13 C16 Tb1 171.6(6) . 2_454 ?
Tb1 O1W H1WA 124.4 . . ?
Tb1 O1W H1WB 110.4 . . ?
H1WA O1W H1WB 124.8 . . ?
H4WA O4W H4WB 88.4 . . ?
C19 N2 C18 123.3(16) . . ?
C19 N2 C17A 171(2) . . ?
C18 N2 C17A 48(2) . . ?
C19 N2 C17 118.7(14) . . ?
C18 N2 C17 118(2) . . ?
C17A N2 C17 70(2) . . ?
C19 N2 C19A 52.6(16) . . ?
C18 N2 C19A 70.8(19) . . ?
C17A N2 C19A 118.4(17) . . ?
C17 N2 C19A 170.3(19) . . ?
C19 N2 C18A 65.3(17) . . ?
C18 N2 C18A 169(2) . . ?
C17A N2 C18A 124(2) . . ?
C17 N2 C18A 54.0(19) . . ?
C19A N2 C18A 117.8(15) . . ?
C19 O7 C19A 67(2) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 N2 121.8(19) . . ?
O7 C19 H19A 119.1 . . ?
N2 C19 H19A 119.1 . . ?
N2 C17A H17D 109.5 . . ?
N2 C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
N2 C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
N2 C18A H18D 109.5 . . ?
N2 C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
N2 C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
O7 C19A N2 116(2) . . ?
O7 C19A H19B 121.8 . . ?
N2 C19A H19B 121.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O7 0.85 1.83 2.59(3) 147.9 .
O1W H1WB O5 0.96 2.08 2.800(9) 131.1 5_556
O4W H4WA O4 0.85 2.21 3.04(5) 165.5 6_556
O4W H4WB O3 0.89 1.89 2.77(5) 178.8 .

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         3.819
_refine_diff_density_min         -3.436
_refine_diff_density_rms         0.207
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1009891'
_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H39 Eu N3 O12.50'
_chemical_formula_weight         841.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   10.959(2)
_cell_length_b                   16.565(3)
_cell_length_c                   19.750(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3585.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9555
_cell_measurement_theta_min      2.0623
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1708
_exptl_absorpt_coefficient_mu    1.816
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8327
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         4599
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23980
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3248
_reflns_number_gt                3132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1045P)²+68.6785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3248
_refine_ls_number_parameters     216
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2089
_refine_ls_wR_factor_gt          0.2048
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4182(10) 0.2500 1.0284(5) 0.025(2) Uani 1 2 d S . .
Eu1 Eu 0.29256(6) 0.2500 0.70399(3) 0.0268(3) Uani 1 2 d S . .
O1 O 0.1861(9) 0.2500 0.8054(4) 0.035(2) Uani 1 2 d S . .
O2 O -0.0076(10) 0.2500 0.8328(6) 0.050(3) Uani 1 2 d S . .
O4 O 0.3428(11) 0.2500 1.1497(5) 0.051(3) Uani 1 2 d S . .
H4A H 0.3493 0.2500 1.1910 0.076 Uiso 1 2 calc SR . .
O3 O 0.1476(13) 0.2500 1.1741(6) 0.064(4) Uani 1 2 d S . .
O5 O 0.3642(7) -0.1439(5) 1.1863(4) 0.046(2) Uani 1 1 d . . .
O6 O 0.2228(8) -0.1547(5) 1.1096(4) 0.052(2) Uani 1 1 d . . .
C1 C 0.1024(12) 0.2500 0.8471(6) 0.025(3) Uani 1 2 d S . .
C2 C 0.1346(12) 0.2500 0.9221(6) 0.027(3) Uani 1 2 d S . .
C3 C 0.0459(13) 0.2500 0.9708(8) 0.038(3) Uani 1 2 d S . .
H3 H -0.0359 0.2500 0.9583 0.046 Uiso 1 2 calc SR . .
C4 C 0.0777(13) 0.2500 1.0388(7) 0.034(3) Uani 1 2 d S . .
H4 H 0.0169 0.2500 1.0716 0.041 Uiso 1 2 calc SR . .
C5 C 0.1997(13) 0.2500 1.0584(7) 0.029(3) Uani 1 2 d S . .
C6 C 0.2908(12) 0.2500 1.0089(7) 0.026(3) Uani 1 2 d S . .
C7 C 0.2557(12) 0.2500 0.9401(6) 0.025(3) Uani 1 2 d S . .
H1 H 0.3153 0.2500 0.9065 0.031 Uiso 1 2 calc SR . .
C8 C 0.2269(16) 0.2500 1.1330(7) 0.041(4) Uani 1 2 d S . .
C9 C 0.4827(9) 0.1761(6) 1.0043(5) 0.032(2) Uani 1 1 d . . .
H9A H 0.5693 0.1814 1.0134 0.039 Uiso 1 1 calc R . .
H9B H 0.4721 0.1710 0.9557 0.039 Uiso 1 1 calc R . .
C10 C 0.4352(9) 0.1006(6) 1.0385(5) 0.031(2) Uani 1 1 d . . .
C11 C 0.4823(11) 0.0764(7) 1.1001(6) 0.046(3) Uani 1 1 d . . .
H11 H 0.5417 0.1079 1.1210 0.055 Uiso 1 1 calc R . .
C12 C 0.4430(10) 0.0068(6) 1.1312(6) 0.041(2) Uani 1 1 d . . .
H12 H 0.4760 -0.0081 1.1728 0.049 Uiso 1 1 calc R . .
C13 C 0.3538(9) -0.0421(6) 1.1009(5) 0.033(2) Uani 1 1 d . . .
C14 C 0.3058(9) -0.0173(6) 1.0391(6) 0.038(2) Uani 1 1 d . . .
H14 H 0.2461 -0.0484 1.0181 0.045 Uiso 1 1 calc R . .
C15 C 0.3461(10) 0.0536(6) 1.0084(5) 0.037(2) Uani 1 1 d . . .
H15 H 0.3127 0.0694 0.9672 0.045 Uiso 1 1 calc R . .
C16 C 0.3126(9) -0.1177(6) 1.1336(5) 0.033(2) Uani 1 1 d . . .
O1W O 0.3912(7) 0.1438(5) 0.7673(5) 0.059(2) Uani 1 1 d . . .
H1WB H 0.4522 0.1652 0.7872 0.070 Uiso 1 1 d R . .
H1WA H 0.3562 0.1141 0.7966 0.070 Uiso 1 1 d R . .
O7 O 0.2422(13) 0.0633(9) 0.8481(8) 0.129(5) Uiso 1 1 d D . .
C17 C 0.1602(14) 0.0180(9) 0.8471(8) 0.110(7) Uiso 1 1 d D . .
N2 N 0.1591(16) -0.0582(10) 0.8147(9) 0.130(7) Uiso 1 1 d D . .
C18 C 0.0454(16) 0.0264(12) 0.8899(11) 0.124(8) Uiso 1 1 d D . .
H18A H -0.0001 0.0743 0.8772 0.148 Uiso 1 1 calc R . .
H18B H 0.0656 0.0296 0.9377 0.148 Uiso 1 1 calc R . .
C20 C 0.045(2) -0.1015(13) 0.8235(13) 0.157(11) Uiso 1 1 d D . .
H20A H 0.0597 -0.1553 0.8410 0.189 Uiso 1 1 calc R . .
H20B H 0.0019 -0.1058 0.7808 0.189 Uiso 1 1 calc R . .
C19 C -0.029(2) -0.0509(17) 0.8745(18) 0.230(18) Uiso 1 1 d D . .
H19A H -0.0423 -0.0815 0.9158 0.276 Uiso 1 1 calc R . .
H19B H -0.1077 -0.0369 0.8555 0.276 Uiso 1 1 calc R . .
O4W O 0.099(3) 0.2500 1.3140(18) 0.091(10) Uiso 0.50 2 d SP . .
H4WA H 0.0224 0.2500 1.3064 0.110 Uiso 0.50 2 d SPR . .
H4WB H 0.1149 0.2500 1.2702 0.110 Uiso 0.50 2 d SPR . .
C21 C 0.248(2) -0.0789(18) 0.7652(15) 0.207(16) Uiso 1 1 d D . .
H21A H 0.3208 -0.0484 0.7729 0.311 Uiso 1 1 calc R . .
H21B H 0.2164 -0.0669 0.7209 0.311 Uiso 1 1 calc R . .
H21C H 0.2657 -0.1355 0.7683 0.311 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.449(16) . ?
N1 C9 1.493(11) 7_565 ?
N1 C9 1.493(11) . ?
Eu1 O2 2.308(10) 6_657 ?
Eu1 O1 2.318(9) . ?
Eu1 O1W 2.415(8) 7_565 ?
Eu1 O1W 2.415(8) . ?
Eu1 O6 2.449(8) 2_554 ?
Eu1 O6 2.449(8) 8_665 ?
Eu1 O5 2.482(7) 2_554 ?
Eu1 O5 2.482(7) 8_665 ?
Eu1 C16 2.840(10) 2_554 ?
Eu1 C16 2.840(10) 8_665 ?
Eu1 H1WB 2.7818 . ?
O1 C1 1.234(16) . ?
O2 C1 1.237(16) . ?
O2 Eu1 2.308(10) 6_557 ?
O4 C8 1.31(2) . ?
O4 H4A 0.8200 . ?
O3 C8 1.19(2) . ?
O5 C16 1.261(12) . ?
O5 Eu1 2.482(7) 2 ?
O6 C16 1.253(13) . ?
O6 Eu1 2.449(8) 2 ?
C1 C2 1.522(17) . ?
C2 C3 1.37(2) . ?
C2 C7 1.374(19) . ?
C3 C4 1.39(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.40(2) . ?
C5 C8 1.504(19) . ?
C6 C7 1.412(18) . ?
C7 H1 0.9300 . ?
C9 C10 1.514(13) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.382(14) . ?
C10 C15 1.384(14) . ?
C11 C12 1.377(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.404(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(14) . ?
C13 C16 1.479(14) . ?
C14 C15 1.394(15) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 Eu1 2.840(10) 2 ?
O1W H1WB 0.8520 . ?
O1W H1WA 0.8502 . ?
O7 C17 1.171(9) . ?
C17 N2 1.416(9) . ?
C17 C18 1.522(9) . ?
N2 C21 1.420(9) . ?
N2 C20 1.451(9) . ?
C18 C19 1.549(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 C19 1.541(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
O4W H4WA 0.8534 . ?
O4W H4WB 0.8810 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C9 111.8(7) . 7_565 ?
C6 N1 C9 111.8(7) . . ?
C9 N1 C9 110.3(10) 7_565 . ?
O2 Eu1 O1 138.6(4) 6_657 . ?
O2 Eu1 O1W 74.8(3) 6_657 7_565 ?
O1 Eu1 O1W 77.1(3) . 7_565 ?
O2 Eu1 O1W 74.8(3) 6_657 . ?
O1 Eu1 O1W 77.1(3) . . ?
O1W Eu1 O1W 93.6(5) 7_565 . ?
O2 Eu1 O6 79.9(3) 6_657 2_554 ?
O1 Eu1 O6 128.6(2) . 2_554 ?
O1W Eu1 O6 153.5(3) 7_565 2_554 ?
O1W Eu1 O6 87.4(3) . 2_554 ?
O2 Eu1 O6 79.9(3) 6_657 8_665 ?
O1 Eu1 O6 128.6(2) . 8_665 ?
O1W Eu1 O6 87.4(3) 7_565 8_665 ?
O1W Eu1 O6 153.5(3) . 8_665 ?
O6 Eu1 O6 80.3(4) 2_554 8_665 ?
O2 Eu1 O5 127.8(2) 6_657 2_554 ?
O1 Eu1 O5 76.9(2) . 2_554 ?
O1W Eu1 O5 154.0(3) 7_565 2_554 ?
O1W Eu1 O5 82.4(3) . 2_554 ?
O6 Eu1 O5 52.3(2) 2_554 2_554 ?
O6 Eu1 O5 107.6(3) 8_665 2_554 ?
O2 Eu1 O5 127.8(2) 6_657 8_665 ?
O1 Eu1 O5 76.9(2) . 8_665 ?
O1W Eu1 O5 82.4(3) 7_565 8_665 ?
O1W Eu1 O5 154.0(3) . 8_665 ?
O6 Eu1 O5 107.6(3) 2_554 8_665 ?
O6 Eu1 O5 52.3(2) 8_665 8_665 ?
O5 Eu1 O5 90.1(4) 2_554 8_665 ?
O2 Eu1 C16 103.4(3) 6_657 2_554 ?
O1 Eu1 C16 102.6(3) . 2_554 ?
O1W Eu1 C16 176.2(3) 7_565 2_554 ?
O1W Eu1 C16 82.7(3) . 2_554 ?
O6 Eu1 C16 26.1(3) 2_554 2_554 ?
O6 Eu1 C16 95.6(3) 8_665 2_554 ?
O5 Eu1 C16 26.3(3) 2_554 2_554 ?
O5 Eu1 C16 101.3(3) 8_665 2_554 ?
O2 Eu1 C16 103.4(3) 6_657 8_665 ?
O1 Eu1 C16 102.6(3) . 8_665 ?
O1W Eu1 C16 82.7(3) 7_565 8_665 ?
O1W Eu1 C16 176.2(3) . 8_665 ?
O6 Eu1 C16 95.6(3) 2_554 8_665 ?
O6 Eu1 C16 26.1(3) 8_665 8_665 ?
O5 Eu1 C16 101.3(3) 2_554 8_665 ?
O5 Eu1 C16 26.3(3) 8_665 8_665 ?
C16 Eu1 C16 101.1(4) 2_554 8_665 ?
O2 Eu1 H1WB 65.8 6_657 . ?
O1 Eu1 H1WB 78.8 . . ?
O1W Eu1 H1WB 77.3 7_565 . ?
O1W Eu1 H1WB 17.1 . . ?
O6 Eu1 H1WB 99.6 2_554 . ?
O6 Eu1 H1WB 145.0 8_665 . ?
O5 Eu1 H1WB 99.3 2_554 . ?
O5 Eu1 H1WB 151.2 8_665 . ?
C16 Eu1 H1WB 98.9 2_554 . ?
C16 Eu1 H1WB 159.1 8_665 . ?
C1 O1 Eu1 162.1(9) . . ?
C1 O2 Eu1 174.8(11) . 6_557 ?
C8 O4 H4A 109.5 . . ?
C16 O5 Eu1 92.9(6) . 2 ?
C16 O6 Eu1 94.7(6) . 2 ?
O1 C1 O2 124.9(12) . . ?
O1 C1 C2 118.5(11) . . ?
O2 C1 C2 116.6(12) . . ?
C3 C2 C7 120.3(13) . . ?
C3 C2 C1 121.3(12) . . ?
C7 C2 C1 118.4(11) . . ?
C2 C3 C4 120.2(13) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.7(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.4(12) . . ?
C4 C5 C8 117.5(13) . . ?
C6 C5 C8 123.1(13) . . ?
C5 C6 C7 118.7(12) . . ?
C5 C6 N1 120.1(12) . . ?
C7 C6 N1 121.2(12) . . ?
C2 C7 C6 120.8(12) . . ?
C2 C7 H1 119.6 . . ?
C6 C7 H1 119.6 . . ?
O3 C8 O4 122.4(14) . . ?
O3 C8 C5 121.7(15) . . ?
O4 C8 C5 115.9(14) . . ?
N1 C9 C10 111.9(8) . . ?
N1 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C15 118.7(9) . . ?
C11 C10 C9 120.2(9) . . ?
C15 C10 C9 121.1(9) . . ?
C12 C11 C10 121.2(10) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.7(10) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 117.9(9) . . ?
C14 C13 C16 121.2(9) . . ?
C12 C13 C16 120.9(9) . . ?
C13 C14 C15 120.7(9) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 120.7(9) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O6 C16 O5 119.7(9) . . ?
O6 C16 C13 119.2(9) . . ?
O5 C16 C13 121.0(9) . . ?
O6 C16 Eu1 59.2(5) . 2 ?
O5 C16 Eu1 60.8(5) . 2 ?
C13 C16 Eu1 172.2(7) . 2 ?
Eu1 O1W H1WB 106.7 . . ?
Eu1 O1W H1WA 124.9 . . ?
H1WB O1W H1WA 106.3 . . ?
O7 C17 N2 125.8(12) . . ?
O7 C17 C18 124.5(12) . . ?
N2 C17 C18 109.0(8) . . ?
C17 N2 C21 121.4(13) . . ?
C17 N2 C20 113.2(9) . . ?
C21 N2 C20 123.5(13) . . ?
C17 C18 C19 104.5(8) . . ?
C17 C18 H18A 110.8 . . ?
C19 C18 H18A 110.8 . . ?
C17 C18 H18B 110.8 . . ?
C19 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
N2 C20 C19 105.3(9) . . ?
N2 C20 H20A 110.7 . . ?
C19 C20 H20A 110.7 . . ?
N2 C20 H20B 110.7 . . ?
C19 C20 H20B 110.7 . . ?
H20A C20 H20B 108.8 . . ?
C20 C19 C18 107.5(9) . . ?
C20 C19 H19A 110.2 . . ?
C18 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
C18 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
H4WA O4W H4WB 91.3 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O7 0.85 1.82 2.644(17) 163.4 .
O1W H1WB O5 0.85 2.11 2.832(11) 142.5 5_657
O4W H4WA O4 0.85 2.15 2.90(4) 146.2 6_558
O4W H4WB O3 0.88 1.93 2.81(4) 179.4 .

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.982
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.194
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1009892'
_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H35 Eu N3 O12.50'
_chemical_formula_weight         813.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   10.9790(4)
_cell_length_b                   16.6505(7)
_cell_length_c                   19.3795(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3542.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10816
_cell_measurement_theta_min      2.1317
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1644
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8401
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         4532
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25850
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3599
_reflns_number_gt                3370
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0759P)²+2.9866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3599
_refine_ls_number_parameters     302
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4186(4) 0.2500 1.0288(2) 0.0295(9) Uani 1 2 d S . .
Eu1 Eu 0.28799(2) 0.2500 0.703641(12) 0.02846(13) Uani 1 2 d S . .
O1 O 0.1796(4) 0.2500 0.80552(19) 0.0410(10) Uani 1 2 d S . .
O2 O -0.0143(4) 0.2500 0.8347(2) 0.0582(12) Uani 1 2 d S . .
O4 O 0.3485(5) 0.2500 1.1538(2) 0.0582(12) Uani 1 2 d S . .
H4A H 0.3572 0.2500 1.1958 0.087 Uiso 1 2 calc SR . .
O3 O 0.1514(5) 0.2500 1.1814(2) 0.0719(15) Uani 1 2 d S . .
O5 O 0.3690(3) -0.14521(19) 1.18412(17) 0.0484(7) Uani 1 1 d . . .
O6 O 0.2233(3) -0.1548(2) 1.10727(19) 0.0572(9) Uani 1 1 d . . .
O1W O 0.3861(3) 0.3545(2) 0.7699(2) 0.0619(9) Uani 1 1 d . . .
H1WB H 0.4610 0.3549 0.7680 0.093 Uiso 1 1 d R . .
H1WA H 0.3408 0.3815 0.7944 0.093 Uiso 1 1 d R . .
C1 C 0.0963(5) 0.2500 0.8488(3) 0.0331(11) Uani 1 2 d S . .
C2 C 0.1308(5) 0.2500 0.9235(3) 0.0348(11) Uani 1 2 d S . .
C3 C 0.0432(6) 0.2500 0.9749(3) 0.0518(16) Uani 1 2 d S . .
H3 H -0.0390 0.2500 0.9633 0.062 Uiso 1 2 calc SR . .
C4 C 0.0783(6) 0.2500 1.0436(3) 0.0497(15) Uani 1 2 d S . .
H4 H 0.0191 0.2500 1.0779 0.060 Uiso 1 2 calc SR . .
C5 C 0.2019(5) 0.2500 1.0621(3) 0.0377(13) Uani 1 2 d S . .
C6 C 0.2879(4) 0.2500 1.0102(3) 0.0287(11) Uani 1 2 d S . .
C7 C 0.2530(5) 0.2500 0.9412(3) 0.0295(10) Uani 1 2 d S . .
H1 H 0.3121 0.2500 0.9067 0.035 Uiso 1 2 calc SR . .
C8 C 0.2295(6) 0.2500 1.1385(3) 0.0472(15) Uani 1 2 d S . .
C9 C 0.4810(4) 0.1764(2) 1.0029(2) 0.0369(8) Uani 1 1 d . . .
H9A H 0.5678 0.1809 1.0115 0.044 Uiso 1 1 calc R . .
H9B H 0.4692 0.1723 0.9534 0.044 Uiso 1 1 calc R . .
C10 C 0.4333(3) 0.1009(2) 1.0372(2) 0.0344(8) Uani 1 1 d . . .
C11 C 0.4814(4) 0.0759(2) 1.0995(2) 0.0464(10) Uani 1 1 d . . .
H11 H 0.5403 0.1071 1.1212 0.056 Uiso 1 1 calc R . .
C12 C 0.4433(4) 0.0057(2) 1.1300(2) 0.0450(10) Uani 1 1 d . . .
H12 H 0.4784 -0.0106 1.1714 0.054 Uiso 1 1 calc R . .
C13 C 0.3545(4) -0.0406(2) 1.10028(19) 0.0347(8) Uani 1 1 d . . .
C14 C 0.3040(4) -0.0156(3) 1.0370(2) 0.0425(10) Uani 1 1 d . . .
H14 H 0.2434 -0.0460 1.0160 0.051 Uiso 1 1 calc R . .
C15 C 0.3447(4) 0.0541(2) 1.0062(2) 0.0415(9) Uani 1 1 d . . .
H15 H 0.3121 0.0698 0.9640 0.050 Uiso 1 1 calc R . .
C16 C 0.3133(4) -0.1178(2) 1.1321(2) 0.0367(8) Uani 1 1 d . . .
N2A N 0.0955(8) 0.5390(5) 0.8352(5) 0.124(3) Uani 0.626(7) 1 d PDU A 1
O7A O 0.2381(6) 0.4422(4) 0.8440(3) 0.073(2) Uani 0.626(7) 1 d PDU A 1
C17A C 0.0439(14) 0.6109(7) 0.8083(6) 0.148(5) Uani 0.626(7) 1 d PDU A 1
H17A H 0.0361 0.6064 0.7591 0.222 Uiso 0.626(7) 1 calc PR A 1
H17B H 0.0960 0.6555 0.8192 0.222 Uiso 0.626(7) 1 calc PR A 1
H17C H -0.0349 0.6194 0.8284 0.222 Uiso 0.626(7) 1 calc PR A 1
C18A C 0.0229(12) 0.4974(9) 0.8894(6) 0.144(5) Uani 0.626(7) 1 d PDU A 1
H18A H -0.0132 0.5365 0.9195 0.216 Uiso 0.626(7) 1 calc PR A 1
H18B H 0.0752 0.4627 0.9157 0.216 Uiso 0.626(7) 1 calc PR A 1
H18C H -0.0401 0.4661 0.8680 0.216 Uiso 0.626(7) 1 calc PR A 1
C19A C 0.2089(9) 0.5040(5) 0.8151(4) 0.105(3) Uani 0.626(7) 1 d PDU A 1
C20A C 0.2700(10) 0.5515(7) 0.7615(5) 0.105(3) Uani 0.626(7) 1 d PDU A 1
H20A H 0.3349 0.5821 0.7818 0.157 Uiso 0.626(7) 1 calc PR A 1
H20B H 0.2124 0.5873 0.7405 0.157 Uiso 0.626(7) 1 calc PR A 1
H20C H 0.3027 0.5161 0.7270 0.157 Uiso 0.626(7) 1 calc PR A 1
N2B N 0.0912(13) 0.5136(8) 0.8568(6) 0.116(3) Uani 0.374(7) 1 d PDU A 2
O7B O 0.2751(15) 0.5000(11) 0.7983(8) 0.123(5) Uani 0.374(7) 1 d PDU A 2
C18B C 0.0763(19) 0.4336(9) 0.8796(10) 0.132(6) Uani 0.374(7) 1 d PDU A 2
H18D H 0.1452 0.4022 0.8655 0.198 Uiso 0.374(7) 1 calc PR A 2
H18E H 0.0035 0.4115 0.8600 0.198 Uiso 0.374(7) 1 calc PR A 2
H18F H 0.0703 0.4329 0.9291 0.198 Uiso 0.374(7) 1 calc PR A 2
C17B C -0.0094(16) 0.5672(12) 0.8784(11) 0.145(5) Uani 0.374(7) 1 d PDU A 2
H17D H -0.0458 0.5467 0.9198 0.217 Uiso 0.374(7) 1 calc PR A 2
H17E H -0.0696 0.5695 0.8425 0.217 Uiso 0.374(7) 1 calc PR A 2
H17F H 0.0220 0.6201 0.8868 0.217 Uiso 0.374(7) 1 calc PR A 2
C19B C 0.1908(14) 0.5444(9) 0.8165(6) 0.105(3) Uani 0.374(7) 1 d PDU A 2
C20B C 0.179(2) 0.6298(9) 0.8012(10) 0.133(6) Uani 0.374(7) 1 d PDU A 2
H20D H 0.1805 0.6598 0.8435 0.199 Uiso 0.374(7) 1 calc PR A 2
H20E H 0.1040 0.6393 0.7775 0.199 Uiso 0.374(7) 1 calc PR A 2
H20F H 0.2461 0.6464 0.7725 0.199 Uiso 0.374(7) 1 calc PR A 2
O4W O 0.6131(16) 0.2500 1.1755(9) 0.114(5) Uiso 0.50 2 d SP . .
H4WA H 0.5350 0.2500 1.1677 0.136 Uiso 0.50 2 d SPR . .
H4WB H 0.6049 0.2864 1.2061 0.136 Uiso 0.25 1 d PR . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.481(6) . ?
N1 C9 1.491(4) . ?
N1 C9 1.491(4) 8_565 ?
Eu1 O2 2.295(4) 6_657 ?
Eu1 O1 2.305(4) . ?
Eu1 O1W 2.415(3) . ?
Eu1 O1W 2.415(3) 8_565 ?
Eu1 O6 2.453(3) 2_554 ?
Eu1 O6 2.453(3) 7_665 ?
Eu1 O5 2.481(3) 2_554 ?
Eu1 O5 2.481(3) 7_665 ?
Eu1 C16 2.829(4) 2_554 ?
Eu1 C16 2.829(4) 7_665 ?
O1 C1 1.241(7) . ?
O2 C1 1.244(7) . ?
O2 Eu1 2.295(4) 6_557 ?
O4 C8 1.340(9) . ?
O4 H4A 0.8200 . ?
O3 C8 1.194(8) . ?
O5 C16 1.264(5) . ?
O5 Eu1 2.481(3) 2 ?
O6 C16 1.260(5) . ?
O6 Eu1 2.453(3) 2 ?
O1W H1WB 0.8238 . ?
O1W H1WA 0.8217 . ?
C1 C2 1.498(7) . ?
C2 C3 1.384(8) . ?
C2 C7 1.384(7) . ?
C3 C4 1.386(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(8) . ?
C5 C8 1.512(8) . ?
C6 C7 1.391(7) . ?
C7 H1 0.9300 . ?
C9 C10 1.515(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.383(6) . ?
C10 C15 1.384(5) . ?
C11 C12 1.375(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.409(6) . ?
C13 C16 1.496(5) . ?
C14 C15 1.379(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 Eu1 2.829(4) 2 ?
N2A C17A 1.424(8) . ?
N2A C19A 1.429(8) . ?
N2A C18A 1.490(9) . ?
O7A C19A 1.215(8) . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C19A C20A 1.469(8) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
N2B C18B 1.413(9) . ?
N2B C19B 1.438(9) . ?
N2B C17B 1.480(9) . ?
O7B C19B 1.236(9) . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C19B C20B 1.458(9) . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
O4W H4WA 0.8704 . ?
O4W H4WB 0.8514 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C9 111.3(3) . . ?
C6 N1 C9 111.3(3) . 8_565 ?
C9 N1 C9 110.6(4) . 8_565 ?
O2 Eu1 O1 139.95(16) 6_657 . ?
O2 Eu1 O1W 75.54(11) 6_657 . ?
O1 Eu1 O1W 76.98(11) . . ?
O2 Eu1 O1W 75.54(11) 6_657 8_565 ?
O1 Eu1 O1W 76.98(11) . 8_565 ?
O1W Eu1 O1W 92.14(19) . 8_565 ?
O2 Eu1 O6 78.55(11) 6_657 2_554 ?
O1 Eu1 O6 128.76(10) . 2_554 ?
O1W Eu1 O6 153.22(11) . 2_554 ?
O1W Eu1 O6 87.82(14) 8_565 2_554 ?
O2 Eu1 O6 78.55(11) 6_657 7_665 ?
O1 Eu1 O6 128.76(10) . 7_665 ?
O1W Eu1 O6 87.82(14) . 7_665 ?
O1W Eu1 O6 153.22(11) 8_565 7_665 ?
O6 Eu1 O6 80.52(18) 2_554 7_665 ?
O2 Eu1 O5 127.43(9) 6_657 2_554 ?
O1 Eu1 O5 76.83(10) . 2_554 ?
O1W Eu1 O5 153.77(11) . 2_554 ?
O1W Eu1 O5 83.35(12) 8_565 2_554 ?
O6 Eu1 O5 52.73(10) 2_554 2_554 ?
O6 Eu1 O5 107.65(12) 7_665 2_554 ?
O2 Eu1 O5 127.43(9) 6_657 7_665 ?
O1 Eu1 O5 76.83(10) . 7_665 ?
O1W Eu1 O5 83.35(12) . 7_665 ?
O1W Eu1 O5 153.77(11) 8_565 7_665 ?
O6 Eu1 O5 107.65(12) 2_554 7_665 ?
O6 Eu1 O5 52.73(10) 7_665 7_665 ?
O5 Eu1 O5 89.37(15) 2_554 7_665 ?
O2 Eu1 C16 102.32(11) 6_657 2_554 ?
O1 Eu1 C16 102.52(11) . 2_554 ?
O1W Eu1 C16 174.90(12) . 2_554 ?
O1W Eu1 C16 82.82(12) 8_565 2_554 ?
O6 Eu1 C16 26.39(11) 2_554 2_554 ?
O6 Eu1 C16 96.32(12) 7_665 2_554 ?
O5 Eu1 C16 26.51(11) 2_554 2_554 ?
O5 Eu1 C16 101.52(11) 7_665 2_554 ?
O2 Eu1 C16 102.32(11) 6_657 7_665 ?
O1 Eu1 C16 102.52(11) . 7_665 ?
O1W Eu1 C16 82.82(12) . 7_665 ?
O1W Eu1 C16 174.90(12) 8_565 7_665 ?
O6 Eu1 C16 96.32(12) 2_554 7_665 ?
O6 Eu1 C16 26.39(11) 7_665 7_665 ?
O5 Eu1 C16 101.52(11) 2_554 7_665 ?
O5 Eu1 C16 26.51(11) 7_665 7_665 ?
C16 Eu1 C16 102.20(16) 2_554 7_665 ?
C1 O1 Eu1 163.5(4) . . ?
C1 O2 Eu1 173.8(4) . 6_557 ?
C8 O4 H4A 109.5 . . ?
C16 O5 Eu1 92.3(2) . 2 ?
C16 O6 Eu1 93.7(3) . 2 ?
Eu1 O1W H1WB 115.3 . . ?
Eu1 O1W H1WA 115.6 . . ?
H1WB O1W H1WA 128.7 . . ?
O1 C1 O2 124.8(5) . . ?
O1 C1 C2 117.8(5) . . ?
O2 C1 C2 117.4(5) . . ?
C3 C2 C7 119.8(5) . . ?
C3 C2 C1 121.3(5) . . ?
C7 C2 C1 119.0(5) . . ?
C2 C3 C4 119.8(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.3(5) . . ?
C6 C5 C8 125.3(5) . . ?
C4 C5 C8 116.4(5) . . ?
C5 C6 C7 120.9(5) . . ?
C5 C6 N1 119.1(5) . . ?
C7 C6 N1 120.1(5) . . ?
C2 C7 C6 120.2(5) . . ?
C2 C7 H1 119.9 . . ?
C6 C7 H1 119.9 . . ?
O3 C8 O4 123.2(6) . . ?
O3 C8 C5 122.5(6) . . ?
O4 C8 C5 114.3(5) . . ?
N1 C9 C10 112.1(3) . . ?
N1 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C15 118.6(4) . . ?
C11 C10 C9 120.0(4) . . ?
C15 C10 C9 121.4(3) . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 118.7(4) . . ?
C12 C13 C16 121.7(4) . . ?
C14 C13 C16 119.6(4) . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 120.9(4) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O6 C16 O5 120.5(4) . . ?
O6 C16 C13 120.0(4) . . ?
O5 C16 C13 119.5(4) . . ?
O6 C16 Eu1 59.9(2) . 2 ?
O5 C16 Eu1 61.2(2) . 2 ?
C13 C16 Eu1 171.8(3) . 2 ?
C17A N2A C19A 126.1(7) . . ?
C17A N2A C18A 115.9(8) . . ?
C19A N2A C18A 118.0(7) . . ?
O7A C19A N2A 116.8(7) . . ?
O7A C19A C20A 131.4(9) . . ?
N2A C19A C20A 111.8(7) . . ?
C18B N2B C19B 126.4(8) . . ?
C18B N2B C17B 113.1(9) . . ?
C19B N2B C17B 120.4(8) . . ?
N2B C18B H18D 109.5 . . ?
N2B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
N2B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
N2B C17B H17D 109.5 . . ?
N2B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
N2B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
O7B C19B N2B 120.8(9) . . ?
O7B C19B C20B 126.1(10) . . ?
N2B C19B C20B 113.1(8) . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
H4WA O4W H4WB 91.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WB O5 0.82 2.09 2.834(4) 150.9 4_657
O1W H1WA O7A 0.82 1.79 2.614(7) 177.1 .
O1W H1WA O7B 0.82 2.10 2.767(16) 138.0 .
O4W H4WA O4 0.87 2.07 2.935(18) 177.5 .
O4W H4WB O3 0.85 2.32 2.804(17) 116.4 6_658

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.310
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.102
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1009893'
_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 Eu N O14.50'
_chemical_formula_weight         715.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   11.048(3)
_cell_length_b                   16.702(4)
_cell_length_c                   18.739(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3457.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8529
_cell_measurement_theta_min      2.1400
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1436
_exptl_absorpt_coefficient_mu    1.872
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7343
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         4432
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23122
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3154
_reflns_number_gt                2905
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1710P)²+7.3308P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3154
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.2155
_refine_ls_wR_factor_gt          0.2081
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4242(7) 0.2500 1.0350(4) 0.0408(17) Uani 1 2 d S . .
Eu1 Eu 0.29712(4) 0.2500 0.70476(2) 0.0386(3) Uani 1 2 d S . .
O1 O 0.1839(7) 0.2500 0.8073(4) 0.056(2) Uani 1 2 d S . .
O2 O -0.0091(6) 0.2500 0.8384(4) 0.066(2) Uani 1 2 d S . .
O4 O 0.3610(9) 0.2500 1.1641(4) 0.069(2) Uani 1 2 d S . .
H4A H 0.3729 0.2500 1.2072 0.104 Uiso 1 2 calc SR . .
O3 O 0.1690(16) 0.2500 1.1959(6) 0.190(13) Uani 1 2 d S . .
O5 O 0.3604(6) -0.1495(4) 1.1818(4) 0.0782(19) Uani 1 1 d . . .
O6 O 0.2118(5) -0.1521(4) 1.1066(4) 0.078(2) Uani 1 1 d . . .
C1 C 0.1007(8) 0.2500 0.8527(5) 0.042(2) Uani 1 2 d S . .
C2 C 0.1391(9) 0.2500 0.9291(5) 0.043(2) Uani 1 2 d S . .
C3 C 0.0527(10) 0.2500 0.9851(7) 0.082(4) Uani 1 2 d S . .
H3 H -0.0294 0.2500 0.9743 0.098 Uiso 1 2 calc SR . .
C4 C 0.0879(11) 0.2500 1.0525(6) 0.090(5) Uani 1 2 d S . .
H4 H 0.0294 0.2500 1.0881 0.108 Uiso 1 2 calc SR . .
C5 C 0.2114(9) 0.2500 1.0722(6) 0.059(3) Uani 1 2 d S . .
C6 C 0.2952(7) 0.2500 1.0185(6) 0.039(2) Uani 1 2 d S . .
C7 C 0.2595(8) 0.2500 0.9454(5) 0.0365(18) Uani 1 2 d S . .
H1 H 0.3174 0.2500 0.9093 0.044 Uiso 1 2 calc SR . .
C8 C 0.2468(17) 0.2500 1.1519(7) 0.086(4) Uani 1 2 d S . .
C9 C 0.4883(6) 0.1754(4) 1.0075(4) 0.0446(15) Uani 1 1 d . . .
H9A H 0.4794 0.1724 0.9561 0.054 Uiso 1 1 calc R . .
H9B H 0.5740 0.1790 1.0183 0.054 Uiso 1 1 calc R . .
C10 C 0.4367(6) 0.1007(4) 1.0411(4) 0.0450(15) Uani 1 1 d . . .
C11 C 0.4718(7) 0.0758(5) 1.1090(4) 0.0571(18) Uani 1 1 d . . .
H11 H 0.5251 0.1069 1.1356 0.068 Uiso 1 1 calc R . .
C12 C 0.4284(7) 0.0064(5) 1.1364(4) 0.0543(18) Uani 1 1 d . . .
H12 H 0.4553 -0.0101 1.1810 0.065 Uiso 1 1 calc R . .
C13 C 0.3464(6) -0.0404(4) 1.1008(4) 0.0445(15) Uani 1 1 d . . .
C14 C 0.3063(6) -0.0158(5) 1.0358(5) 0.0528(19) Uani 1 1 d . . .
H14 H 0.2480 -0.0458 1.0120 0.063 Uiso 1 1 calc R . .
C15 C 0.3518(7) 0.0548(4) 1.0037(4) 0.0486(16) Uani 1 1 d . . .
H15 H 0.3257 0.0703 0.9586 0.058 Uiso 1 1 calc R . .
C16 C 0.3042(6) -0.1176(5) 1.1310(4) 0.0507(19) Uani 1 1 d . . .
O1W O 0.3941(6) 0.1489(5) 0.7753(4) 0.086(2) Uani 1 1 d . . .
H1WB H 0.4784 0.1447 0.7621 0.130 Uiso 1 1 d R . .
H1WA H 0.3893 0.1607 0.8227 0.130 Uiso 1 1 d R . .
O2W O 0.7666(12) -0.0396(8) 1.1677(7) 0.150(4) Uiso 1 1 d . . .
H2WA H 0.8390 -0.0389 1.1447 0.181 Uiso 1 1 d R . .
H2WB H 0.7137 -0.0721 1.1873 0.181 Uiso 1 1 d R . .
O3W O 0.9794(19) -0.0443(18) 1.1065(14) 0.307(12) Uiso 1 1 d . . .
H3WC H 1.0266 -0.0473 1.1422 0.369 Uiso 1 1 d R . .
H3WB H 1.0252 -0.0646 1.0749 0.369 Uiso 1 1 d R . .
O4W O 0.668(3) 0.2500 1.1443(17) 0.133(10) Uiso 0.50 2 d SP . .
H4WA H 0.5905 0.2500 1.1471 0.160 Uiso 0.50 2 d SPR . .
H4WB H 0.6746 0.2865 1.1754 0.160 Uiso 0.25 1 d PR . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.459(10) . ?
N1 C9 1.522(8) . ?
N1 C9 1.522(8) 7_565 ?
Eu1 O2 2.288(7) 6_657 ?
Eu1 O1 2.294(8) . ?
Eu1 O1W 2.398(6) 7_565 ?
Eu1 O1W 2.398(6) . ?
Eu1 O5 2.456(6) 2_554 ?
Eu1 O5 2.456(6) 8_665 ?
Eu1 O6 2.463(6) 2_554 ?
Eu1 O6 2.463(6) 8_665 ?
Eu1 C16 2.839(8) 2_554 ?
Eu1 C16 2.839(8) 8_665 ?
O1 C1 1.252(12) . ?
O2 C1 1.243(11) . ?
O2 Eu1 2.288(7) 6_557 ?
O4 C8 1.28(2) . ?
O4 H4A 0.8200 . ?
O3 C8 1.19(2) . ?
O5 C16 1.256(10) . ?
O5 Eu1 2.456(6) 2 ?
O6 C16 1.258(9) . ?
O6 Eu1 2.463(6) 2 ?
C1 C2 1.492(13) . ?
C2 C7 1.365(14) . ?
C2 C3 1.418(14) . ?
C3 C4 1.321(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.414(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(14) . ?
C5 C8 1.544(18) . ?
C6 C7 1.425(14) . ?
C7 H1 0.9300 . ?
C9 C10 1.510(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.393(10) . ?
C10 C15 1.400(10) . ?
C11 C12 1.355(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(11) . ?
C13 C16 1.482(11) . ?
C14 C15 1.415(11) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 Eu1 2.839(8) 2 ?
O1W H1WB 0.9672 . ?
O1W H1WA 0.9117 . ?
O2W H2WA 0.9087 . ?
O2W H2WB 0.8780 . ?
O3W H3WC 0.8490 . ?
O3W H3WB 0.8496 . ?
O4W H4WA 0.8621 . ?
O4W H4WB 0.8466 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C9 112.5(5) . . ?
C6 N1 C9 112.5(5) . 7_565 ?
C9 N1 C9 109.8(7) . 7_565 ?
O2 Eu1 O1 143.8(3) 6_657 . ?
O2 Eu1 O1W 77.1(2) 6_657 7_565 ?
O1 Eu1 O1W 77.4(2) . 7_565 ?
O2 Eu1 O1W 77.1(2) 6_657 . ?
O1 Eu1 O1W 77.4(2) . . ?
O1W Eu1 O1W 89.6(4) 7_565 . ?
O2 Eu1 O5 126.94(17) 6_657 2_554 ?
O1 Eu1 O5 76.1(2) . 2_554 ?
O1W Eu1 O5 153.5(2) 7_565 2_554 ?
O1W Eu1 O5 86.1(3) . 2_554 ?
O2 Eu1 O5 126.94(18) 6_657 8_665 ?
O1 Eu1 O5 76.1(2) . 8_665 ?
O1W Eu1 O5 86.1(3) 7_565 8_665 ?
O1W Eu1 O5 153.5(2) . 8_665 ?
O5 Eu1 O5 86.2(4) 2_554 8_665 ?
O2 Eu1 O6 76.9(2) 6_657 2_554 ?
O1 Eu1 O6 127.16(17) . 2_554 ?
O1W Eu1 O6 153.8(2) 7_565 2_554 ?
O1W Eu1 O6 87.9(3) . 2_554 ?
O5 Eu1 O6 52.19(19) 2_554 2_554 ?
O5 Eu1 O6 107.1(3) 8_665 2_554 ?
O2 Eu1 O6 76.9(2) 6_657 8_665 ?
O1 Eu1 O6 127.16(17) . 8_665 ?
O1W Eu1 O6 87.9(3) 7_565 8_665 ?
O1W Eu1 O6 153.8(2) . 8_665 ?
O5 Eu1 O6 107.1(3) 2_554 8_665 ?
O5 Eu1 O6 52.19(19) 8_665 8_665 ?
O6 Eu1 O6 83.1(4) 2_554 8_665 ?
O2 Eu1 C16 101.34(18) 6_657 2_554 ?
O1 Eu1 C16 101.1(2) . 2_554 ?
O1W Eu1 C16 173.6(3) 7_565 2_554 ?
O1W Eu1 C16 84.0(3) . 2_554 ?
O5 Eu1 C16 26.2(2) 2_554 2_554 ?
O5 Eu1 C16 99.7(2) 8_665 2_554 ?
O6 Eu1 C16 26.2(2) 2_554 2_554 ?
O6 Eu1 C16 97.9(3) 8_665 2_554 ?
O2 Eu1 C16 101.34(18) 6_657 8_665 ?
O1 Eu1 C16 101.1(2) . 8_665 ?
O1W Eu1 C16 84.0(3) 7_565 8_665 ?
O1W Eu1 C16 173.6(3) . 8_665 ?
O5 Eu1 C16 99.7(2) 2_554 8_665 ?
O5 Eu1 C16 26.2(2) 8_665 8_665 ?
O6 Eu1 C16 97.9(3) 2_554 8_665 ?
O6 Eu1 C16 26.25(19) 8_665 8_665 ?
C16 Eu1 C16 102.4(3) 2_554 8_665 ?
C1 O1 Eu1 165.9(7) . . ?
C1 O2 Eu1 171.8(7) . 6_557 ?
C8 O4 H4A 109.5 . . ?
C16 O5 Eu1 94.2(5) . 2 ?
C16 O6 Eu1 93.8(5) . 2 ?
O2 C1 O1 124.7(9) . . ?
O2 C1 C2 119.0(8) . . ?
O1 C1 C2 116.3(8) . . ?
C7 C2 C3 119.4(9) . . ?
C7 C2 C1 119.4(8) . . ?
C3 C2 C1 121.2(9) . . ?
C4 C3 C2 120.6(11) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 122.3(10) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 117.4(10) . . ?
C6 C5 C8 122.7(11) . . ?
C4 C5 C8 119.8(11) . . ?
C5 C6 C7 121.3(8) . . ?
C5 C6 N1 120.3(9) . . ?
C7 C6 N1 118.3(8) . . ?
C2 C7 C6 119.0(8) . . ?
C2 C7 H1 120.5 . . ?
C6 C7 H1 120.5 . . ?
O3 C8 O4 126.0(15) . . ?
O3 C8 C5 119.1(17) . . ?
O4 C8 C5 114.9(11) . . ?
C10 C9 N1 111.1(5) . . ?
C10 C9 H9A 109.4 . . ?
N1 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
N1 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C15 118.7(7) . . ?
C11 C10 C9 121.4(6) . . ?
C15 C10 C9 119.8(6) . . ?
C12 C11 C10 120.1(7) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 122.6(7) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C14 C13 C12 118.6(7) . . ?
C14 C13 C16 120.1(7) . . ?
C12 C13 C16 121.3(7) . . ?
C13 C14 C15 121.2(7) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 118.7(7) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
O5 C16 O6 118.8(8) . . ?
O5 C16 C13 120.2(7) . . ?
O6 C16 C13 121.1(7) . . ?
O5 C16 Eu1 59.6(4) . 2 ?
O6 C16 Eu1 60.0(4) . 2 ?
C13 C16 Eu1 170.8(5) . 2 ?
Eu1 O1W H1WB 109.8 . . ?
Eu1 O1W H1WA 111.0 . . ?
H1WB O1W H1WA 108.7 . . ?
H2WA O2W H2WB 142.3 . . ?
H3WC O3W H3WB 99.2 . . ?
H4WA O4W H4WB 92.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WB O5 0.97 2.07 2.829(9) 134.1 5_657
O2W H2WA O3W 0.91 1.71 2.62(2) 174.9 .
O2W H2WB O1W 0.88 1.89 2.761(16) 175.1 5_657
O4W H4WA O4 0.86 2.56 3.42(4) 176.3 .
O4W H4WB O3 0.85 2.49 3.00(3) 119.3 6_658

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.607
_refine_diff_density_min         -0.998
_refine_diff_density_rms         0.192
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1010141'
_audit_update_record             
;
2014-06-25 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H35 N3 O12.50 Tb'
_chemical_formula_weight         820.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   10.929
_cell_length_b                   16.586
_cell_length_c                   19.396
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3515.9
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10619
_cell_measurement_theta_min      2.1391
_cell_measurement_theta_max      27.4816

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1652
_exptl_absorpt_coefficient_mu    2.077
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8512
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         4502
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24395
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3569
_reflns_number_gt                3438
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0715P)²+5.6415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3569
_refine_ls_number_parameters     302
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4179(4) 0.2500 1.0282(2) 0.0283(10) Uani 1 2 d S . .
Tb1 Tb 0.28820(2) 0.2500 0.704068(14) 0.02757(13) Uani 1 2 d S . .
O1 O 0.1804(5) 0.2500 0.8046(2) 0.0408(11) Uani 1 2 d S . .
O2 O -0.0143(4) 0.2500 0.8327(3) 0.0554(14) Uani 1 2 d S . .
O4 O 0.3467(5) 0.2500 1.1526(3) 0.0549(14) Uani 1 2 d S . .
H4A H 0.3548 0.2500 1.1946 0.082 Uiso 1 2 calc SR . .
O3 O 0.1496(6) 0.2500 1.1801(3) 0.0694(18) Uani 1 2 d S . .
O5 O 0.3685(3) -0.1464(2) 1.18462(19) 0.0482(9) Uani 1 1 d . . .
O6 O 0.2223(3) -0.1557(2) 1.1086(2) 0.0573(11) Uani 1 1 d . . .
O1W O 0.3849(3) 0.3537(3) 0.7690(2) 0.0597(11) Uani 1 1 d . . .
H1WB H 0.4599 0.3541 0.7670 0.090 Uiso 1 1 d R . .
H1WA H 0.3397 0.3808 0.7935 0.090 Uiso 1 1 d R . .
C1 C 0.0956(5) 0.2500 0.8475(3) 0.0317(13) Uani 1 2 d S . .
C2 C 0.1301(5) 0.2500 0.9226(3) 0.0331(13) Uani 1 2 d S . .
C3 C 0.0415(6) 0.2500 0.9735(4) 0.0502(19) Uani 1 2 d S . .
H3 H -0.0409 0.2500 0.9617 0.060 Uiso 1 2 calc SR . .
C4 C 0.0765(7) 0.2500 1.0423(4) 0.0488(18) Uani 1 2 d S . .
H4 H 0.0169 0.2500 1.0765 0.059 Uiso 1 2 calc SR . .
C5 C 0.1999(6) 0.2500 1.0607(3) 0.0360(14) Uani 1 2 d S . .
C6 C 0.2869(5) 0.2500 1.0095(3) 0.0274(12) Uani 1 2 d S . .
C7 C 0.2527(5) 0.2500 0.9401(3) 0.0269(11) Uani 1 2 d S . .
H1 H 0.3121 0.2500 0.9059 0.032 Uiso 1 2 calc SR . .
C8 C 0.2289(7) 0.2500 1.1370(4) 0.0460(17) Uani 1 2 d S . .
C9 C 0.4812(4) 0.1759(3) 1.0024(2) 0.0364(10) Uani 1 1 d . . .
H9A H 0.5684 0.1807 1.0110 0.044 Uiso 1 1 calc R . .
H9B H 0.4692 0.1715 0.9530 0.044 Uiso 1 1 calc R . .
C10 C 0.4335(4) 0.1002(3) 1.0373(2) 0.0345(9) Uani 1 1 d . . .
C11 C 0.4819(5) 0.0754(3) 1.0995(3) 0.0452(12) Uani 1 1 d . . .
H11 H 0.5408 0.1069 1.1212 0.054 Uiso 1 1 calc R . .
C12 C 0.4441(5) 0.0048(3) 1.1298(3) 0.0448(11) Uani 1 1 d . . .
H12 H 0.4801 -0.0120 1.1708 0.054 Uiso 1 1 calc R . .
C13 C 0.3539(4) -0.0412(2) 1.1003(2) 0.0332(9) Uani 1 1 d . . .
C14 C 0.3031(4) -0.0165(3) 1.0381(3) 0.0422(11) Uani 1 1 d . . .
H14 H 0.2420 -0.0472 1.0175 0.051 Uiso 1 1 calc R . .
C15 C 0.3431(4) 0.0534(3) 1.0067(2) 0.0398(10) Uani 1 1 d . . .
H15 H 0.3093 0.0693 0.9649 0.048 Uiso 1 1 calc R . .
C16 C 0.3130(4) -0.1187(3) 1.1329(2) 0.0350(10) Uani 1 1 d . . .
N2A N 0.0968(9) 0.5407(6) 0.8358(5) 0.126(3) Uani 0.654(8) 1 d PDU A 1
O7A O 0.2390(7) 0.4424(4) 0.8438(4) 0.075(2) Uani 0.654(8) 1 d PDU A 1
C17A C 0.0473(15) 0.6133(7) 0.8083(7) 0.146(5) Uani 0.654(8) 1 d PDU A 1
H17A H 0.0506 0.6115 0.7588 0.219 Uiso 0.654(8) 1 calc PR A 1
H17B H 0.0940 0.6584 0.8246 0.219 Uiso 0.654(8) 1 calc PR A 1
H17C H -0.0363 0.6189 0.8228 0.219 Uiso 0.654(8) 1 calc PR A 1
C18A C 0.0244(13) 0.5002(10) 0.8902(6) 0.144(5) Uani 0.654(8) 1 d PDU A 1
H18A H 0.0133 0.5364 0.9284 0.217 Uiso 0.654(8) 1 calc PR A 1
H18B H 0.0669 0.4529 0.9056 0.217 Uiso 0.654(8) 1 calc PR A 1
H18C H -0.0540 0.4852 0.8720 0.217 Uiso 0.654(8) 1 calc PR A 1
C19A C 0.2101(9) 0.5044(5) 0.8150(4) 0.110(3) Uani 0.654(8) 1 d PDU A 1
C20A C 0.2706(12) 0.5515(8) 0.7609(6) 0.111(4) Uani 0.654(8) 1 d PDU A 1
H20A H 0.3362 0.5823 0.7808 0.166 Uiso 0.654(8) 1 calc PR A 1
H20B H 0.2125 0.5874 0.7401 0.166 Uiso 0.654(8) 1 calc PR A 1
H20C H 0.3029 0.5157 0.7265 0.166 Uiso 0.654(8) 1 calc PR A 1
N2B N 0.0923(16) 0.5138(11) 0.8559(8) 0.119(4) Uani 0.346(8) 1 d PDU A 2
O7B O 0.2736(18) 0.5003(14) 0.7938(10) 0.125(5) Uani 0.346(8) 1 d PDU A 2
C18B C 0.078(2) 0.4332(12) 0.8782(13) 0.136(7) Uani 0.346(8) 1 d PDU A 2
H18D H 0.1491 0.4026 0.8659 0.204 Uiso 0.346(8) 1 calc PR A 2
H18E H 0.0071 0.4101 0.8564 0.204 Uiso 0.346(8) 1 calc PR A 2
H18F H 0.0673 0.4322 0.9273 0.204 Uiso 0.346(8) 1 calc PR A 2
C17B C -0.006(2) 0.5682(16) 0.8795(13) 0.143(6) Uani 0.346(8) 1 d PDU A 2
H17D H -0.0233 0.5577 0.9272 0.214 Uiso 0.346(8) 1 calc PR A 2
H17E H -0.0783 0.5590 0.8526 0.214 Uiso 0.346(8) 1 calc PR A 2
H17F H 0.0198 0.6232 0.8742 0.214 Uiso 0.346(8) 1 calc PR A 2
C19B C 0.1909(17) 0.5443(11) 0.8141(7) 0.111(4) Uani 0.346(8) 1 d PDU A 2
C20B C 0.179(3) 0.6305(11) 0.8002(12) 0.131(7) Uani 0.346(8) 1 d PDU A 2
H20D H 0.1840 0.6600 0.8427 0.197 Uiso 0.346(8) 1 calc PR A 2
H20E H 0.1009 0.6408 0.7789 0.197 Uiso 0.346(8) 1 calc PR A 2
H20F H 0.2430 0.6475 0.7698 0.197 Uiso 0.346(8) 1 calc PR A 2
O4W O 0.6140(17) 0.2500 1.1752(10) 0.107(5) Uiso 0.50 2 d SP . .
H4WA H 0.5359 0.2500 1.1674 0.129 Uiso 0.50 2 d SPR . .
H4WB H 0.6058 0.2864 1.2058 0.129 Uiso 0.25 1 d PR . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.477(7) . ?
N1 C9 1.496(5) 8_565 ?
N1 C9 1.496(5) . ?
Tb1 O2 2.273(4) 6_657 ?
Tb1 O1 2.277(5) . ?
Tb1 O1W 2.379(4) . ?
Tb1 O1W 2.379(4) 8_565 ?
Tb1 O6 2.426(4) 2_554 ?
Tb1 O6 2.426(4) 7_665 ?
Tb1 O5 2.455(3) 2_554 ?
Tb1 O5 2.455(3) 7_665 ?
Tb1 C16 2.805(5) 2_554 ?
Tb1 C16 2.805(5) 7_665 ?
O1 C1 1.246(8) . ?
O2 C1 1.235(7) . ?
O2 Tb1 2.273(4) 6_557 ?
O4 C8 1.322(10) . ?
O4 H4A 0.8200 . ?
O3 C8 1.204(9) . ?
O5 C16 1.259(6) . ?
O5 Tb1 2.455(3) 2 ?
O6 C16 1.256(6) . ?
O6 Tb1 2.426(4) 2 ?
O1W H1WB 0.8200 . ?
O1W H1WA 0.8196 . ?
C1 C2 1.506(8) . ?
C2 C3 1.381(9) . ?
C2 C7 1.382(8) . ?
C3 C4 1.389(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(9) . ?
C5 C8 1.513(9) . ?
C6 C7 1.396(8) . ?
C7 H1 0.9300 . ?
C9 C10 1.519(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.381(7) . ?
C10 C15 1.388(6) . ?
C11 C12 1.375(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(6) . ?
C13 C16 1.501(6) . ?
C14 C15 1.381(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 Tb1 2.805(5) 2 ?
N2A C17A 1.424(9) . ?
N2A C19A 1.435(8) . ?
N2A C18A 1.481(9) . ?
O7A C19A 1.214(8) . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C19A C20A 1.465(8) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
N2B C18B 1.414(9) . ?
N2B C19B 1.440(9) . ?
N2B C17B 1.475(10) . ?
O7B C19B 1.226(9) . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C19B C20B 1.462(9) . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
O4W H4WA 0.8665 . ?
O4W H4WB 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C9 111.5(3) . 8_565 ?
C6 N1 C9 111.5(3) . . ?
C9 N1 C9 110.4(5) 8_565 . ?
O2 Tb1 O1 139.43(19) 6_657 . ?
O2 Tb1 O1W 75.16(12) 6_657 . ?
O1 Tb1 O1W 77.13(13) . . ?
O2 Tb1 O1W 75.16(12) 6_657 8_565 ?
O1 Tb1 O1W 77.13(13) . 8_565 ?
O1W Tb1 O1W 92.6(2) . 8_565 ?
O2 Tb1 O6 78.80(13) 6_657 2_554 ?
O1 Tb1 O6 128.93(11) . 2_554 ?
O1W Tb1 O6 152.97(12) . 2_554 ?
O1W Tb1 O6 87.62(16) 8_565 2_554 ?
O2 Tb1 O6 78.80(13) 6_657 7_665 ?
O1 Tb1 O6 128.93(11) . 7_665 ?
O1W Tb1 O6 87.62(16) . 7_665 ?
O1W Tb1 O6 152.97(12) 8_565 7_665 ?
O6 Tb1 O6 80.3(2) 2_554 7_665 ?
O2 Tb1 O5 127.88(10) 6_657 2_554 ?
O1 Tb1 O5 76.74(12) . 2_554 ?
O1W Tb1 O5 153.80(13) . 2_554 ?
O1W Tb1 O5 83.40(14) 8_565 2_554 ?
O6 Tb1 O5 53.01(11) 2_554 2_554 ?
O6 Tb1 O5 107.52(15) 7_665 2_554 ?
O2 Tb1 O5 127.88(10) 6_657 7_665 ?
O1 Tb1 O5 76.74(12) . 7_665 ?
O1W Tb1 O5 83.40(14) . 7_665 ?
O1W Tb1 O5 153.80(13) 8_565 7_665 ?
O6 Tb1 O5 107.52(15) 2_554 7_665 ?
O6 Tb1 O5 53.01(11) 7_665 7_665 ?
O5 Tb1 O5 88.86(18) 2_554 7_665 ?
O2 Tb1 C16 102.71(12) 6_657 2_554 ?
O1 Tb1 C16 102.55(12) . 2_554 ?
O1W Tb1 C16 175.31(14) . 2_554 ?
O1W Tb1 C16 82.78(14) 8_565 2_554 ?
O6 Tb1 C16 26.55(13) 2_554 2_554 ?
O6 Tb1 C16 96.09(15) 7_665 2_554 ?
O5 Tb1 C16 26.64(12) 2_554 2_554 ?
O5 Tb1 C16 101.11(13) 7_665 2_554 ?
O2 Tb1 C16 102.71(12) 6_657 7_665 ?
O1 Tb1 C16 102.55(12) . 7_665 ?
O1W Tb1 C16 82.78(14) . 7_665 ?
O1W Tb1 C16 175.31(14) 8_565 7_665 ?
O6 Tb1 C16 96.09(15) 2_554 7_665 ?
O6 Tb1 C16 26.55(13) 7_665 7_665 ?
O5 Tb1 C16 101.11(13) 2_554 7_665 ?
O5 Tb1 C16 26.64(12) 7_665 7_665 ?
C16 Tb1 C16 101.81(18) 2_554 7_665 ?
C1 O1 Tb1 163.1(4) . . ?
C1 O2 Tb1 175.2(5) . 6_557 ?
C8 O4 H4A 109.5 . . ?
C16 O5 Tb1 92.4(3) . 2 ?
C16 O6 Tb1 93.8(3) . 2 ?
Tb1 O1W H1WB 115.2 . . ?
Tb1 O1W H1WA 115.7 . . ?
H1WB O1W H1WA 128.7 . . ?
O2 C1 O1 124.6(6) . . ?
O2 C1 C2 118.0(5) . . ?
O1 C1 C2 117.4(5) . . ?
C3 C2 C7 120.2(6) . . ?
C3 C2 C1 121.0(6) . . ?
C7 C2 C1 118.7(5) . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.9(6) . . ?
C6 C5 C8 124.1(6) . . ?
C4 C5 C8 116.9(6) . . ?
C5 C6 C7 120.7(5) . . ?
C5 C6 N1 119.5(5) . . ?
C7 C6 N1 119.7(5) . . ?
C2 C7 C6 119.8(6) . . ?
C2 C7 H1 120.1 . . ?
C6 C7 H1 120.1 . . ?
O3 C8 O4 122.8(7) . . ?
O3 C8 C5 121.9(7) . . ?
O4 C8 C5 115.3(6) . . ?
N1 C9 C10 111.8(3) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C15 118.6(4) . . ?
C11 C10 C9 120.2(4) . . ?
C15 C10 C9 121.1(4) . . ?
C12 C11 C10 120.9(5) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.0(4) . . ?
C12 C13 C16 121.0(4) . . ?
C14 C13 C16 119.9(4) . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.5(4) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
O6 C16 O5 120.0(4) . . ?
O6 C16 C13 119.7(4) . . ?
O5 C16 C13 120.3(4) . . ?
O6 C16 Tb1 59.7(2) . 2 ?
O5 C16 Tb1 61.0(2) . 2 ?
C13 C16 Tb1 171.7(3) . 2 ?
C17A N2A C19A 125.3(8) . . ?
C17A N2A C18A 116.6(8) . . ?
C19A N2A C18A 118.2(7) . . ?
O7A C19A N2A 116.8(8) . . ?
O7A C19A C20A 131.7(9) . . ?
N2A C19A C20A 111.6(7) . . ?
C18B N2B C19B 126.0(8) . . ?
C18B N2B C17B 113.7(9) . . ?
C19B N2B C17B 120.3(8) . . ?
N2B C18B H18D 109.5 . . ?
N2B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
N2B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
N2B C17B H17D 109.5 . . ?
N2B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
N2B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
O7B C19B N2B 121.6(9) . . ?
O7B C19B C20B 126.2(10) . . ?
N2B C19B C20B 112.3(8) . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
H4WA O4W H4WB 91.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WB O5 0.82 2.10 2.842(5) 150.8 4_657
O1W H1WA O7A 0.82 1.79 2.611(8) 177.6 .
O1W H1WA O7B 0.82 2.11 2.76(2) 136.3 .
O4W H4WA O4 0.87 2.09 2.954(19) 177.9 .
O4W H4WB O3 0.85 2.34 2.83(2) 117.0 6_658

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.508
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.105
